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Personal Finance Advice and Education! (2 Viewers)

Random thoughts of an older guy that has learned from some small errors ...background ... we are fairly fortunate. not top 1%, but maybe top 3%. Put 2 kids through college. Mid-50s and could retire but will keep working for another 5-10 years mostly to cover the cost of medical insurance since we are self-employed and we'd be bored if we didn't have any work to do.

Here's some things I wish I had done different ... and I'll caveat I am not an investment professional. Just feel like we as little people get duped into a few things.

1) buy a house earlier, and pay it off fast. The latter part is not what many experts will tell you. They'll say spread those payments as long as possible and invest your extra instead. And we have a low interest rate of 2.75%. But the freedom of mind for having a paid off house is enormous when it comes to retirement and making decisions later in life. If you happen to pay it off fast, you can then buy rental properties or rent your own place or make more investments. The freedom of no mortgage is more important than the few extra bucks you might make investing You know who tells you to not pay it off? Investment professionals that make money off your investments. Get a 30 year loan to keep the stress down, and try to pay 10% more per payment. Amazing how much you will save in interest. And your investment is in an appreciating asset.

2) do not maximize 401k / IRA plans - I look back on them and almost think it's almost a scam. Why? You do not know the tax rate when you need those funds. And your money is not liquid until you hit age >59, and more likely age 65 or so. In theory you will make less at age 65 when pulling it out than you will in your working years. But what if the tax rate doubles when you take it out? Or you need it earlier? Or the govt changes the rules? It's tied up as part of the system. And you don't control it Do however put in the max for your corporate match. That's free money. Take the free money.

3. Use 529 plans - Why these but not the 401k? Because you are going to use the 529 much earlier in life. And you are gonna pay for college if you have kids so get it out of the way ASAP. It will really help them get off your payroll if they don't have college debt. It's an ease of mind thing to know it's paid for early on.

4. Do not use an investment advisor unless you have more than the inheritance tax threshold. Why? Even if your professional is cheap at like $5k/year ... amortize that over 30 years at the S&P growth rate of 8%. It's almost $700,000 you've paid for that "advice" which is really just an investment mix in one of their standard portfolios. Now once you hit the inheritance threshold, you need legal advice to create trusts and other tax avoidance strategies. That is worth paying for to help the next generation. But $700K in costs for the potential to make 1-2% more in the advisors "investment mix" is not worth the risk.

5. Put all your stock investments into the S%P 500 index fund or a mix of the S&P large, mid, and small caps - Why? It's a great return in the long run. And you do not know more than everyone else. And you certainly don't know more than large firms helping the super wealthy with hundreds of computers figuring it out. Warren Buffett also backs this strategy. If you want play money for crypto or a few individual stocks for fun ... hey live a little. But you are not going to outsmart the system. Just ride the wave that is the US Economy.

6. As odd as it sounds since it's a bad investment, I wish we had signed up for a universal life insurance plan. We did term insurance. Sure it's cheap. It will also go away in a couple of years, or get prohibitively expensive. The ULI would have been better as I look back. It has really helped a few friends that lost spouses. At worst someone is getting a lump sum payout at a low savings rate.

7. If possible, never sell your houses - If you are forced to move, rent your current house and save up for the downpayment on the next. Most of our super wealthy friends have 5-10 homes. They have the dump they started in, then a few move up homes. And they are pulling in $4-8K per house (big metro area). And a few are paid off, so it's pure income other than the taxes and insurance. One of my buddies make $34K/month on rentals where he has paid off the homes. That is living my friends. We sold our $125K TH 25 years ago because we needed the $20K down for the next house. That TH is now worth $680K. What a dumb decision, all to get a smaller payment on the next house. Find a way to hold rather than sell your real estate assets.

8. Teach your kids a budget - our kids are smart and thifty and luckily doing great. they also were not worldly when it came to money. Like what groceries, cars, houses, etc cost Or even what we paid for. Like they had no idea what home or car insurance was. They have learned quickly since getting out of college.. Sit down with them and show them your budget at like ages 11-14. My wife did not want them to know what we made. It's important they understand so they appreciate the value of a good job

9. Earnings potential is so important - When I met my wife I was doing just fine in computer jobs. She was in sales. If you want to make money you need a job that has high potential earnings. You can be very comfy in a normal 8-6 job. Which keeps you up with the Joneses. You want to exceed the standard? It's not an 8-6 job. It a full time, 24 hour, work your *** job and earn commissions or stock incentives or run your own business job. It's not for everyone. But limited income = limited wealth.

I'm sure there are more. But these are the ones I've been stewing through as I look back on my first 50 years.
 
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2) do not maximize 401k / IRA plans - I look back on them and almost think it's almost a scam. Why? You do not know the tax rate when you need those funds. And your money is not liquid until you hit age >59, and more likely age 65 or so. In theory you will make less at age 65 when pulling it out than you will in your working years. But what if the tax rate doubles when you take it out? Or you need it earlier? Or the govt changes the rules? It's tied up as part of the system. And you don't control it

Excellent list! I do quibble with this one. I don’t think you are valuing the advantage of saving on taxes earlier. Those tax savings can be invested and grown for decades during your working years. This can be significant.

Roths can be extremely valuable too but I don’t think you’re f referring to them.
 
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2) do not maximize 401k / IRA plans - I look back on them and almost think it's almost a scam. Why? You do not know the tax rate when you need those funds. And your money is not liquid until you hit age >59, and more likely age 65 or so. In theory you will make less at age 65 when pulling it out than you will in your working years. But what if the tax rate doubles when you take it out? Or you need it earlier? Or the govt changes the rules? It's tied up as part of the system. And you don't control it Do however put in the max for your corporate match. That's free money. Take the free money.
Disagree strongly here. There are a few ways to access your money earlier and, if you do it right, you could end up never paying taxes on these funds.
 
My 2.75% 30 year fixed is free money right now. No way I'm paying it off early or adding extra payments.
I'm trying desperately to keep my 2.75% with 15 years left on the note, but finding landlord insurance while I'm not residing in the country is proving very problematic. I really don't want to sell the house and have to figure out where to park the cap gains and not get a huge tax bill.
When did you last live there? You would likely be able to avoid capital gains on a sale under the 2 out of 5 rule.
I'm still living there now. Have been for 10 years. Converting it to a rental while I live outside the US.
 
My 2.75% 30 year fixed is free money right now. No way I'm paying it off early or adding extra payments.
I'm trying desperately to keep my 2.75% with 15 years left on the note, but finding landlord insurance while I'm not residing in the country is proving very problematic. I really don't want to sell the house and have to figure out where to park the cap gains and not get a huge tax bill.
Insurance is not my strong point but have you tried talking to an insurance broker versus captive agents?
I'm working with a broker now. He said he's down to 1 option left for me.
 
My 2.75% 30 year fixed is free money right now. No way I'm paying it off early or adding extra payments.
I'm trying desperately to keep my 2.75% with 15 years left on the note, but finding landlord insurance while I'm not residing in the country is proving very problematic. I really don't want to sell the house and have to figure out where to park the cap gains and not get a huge tax bill.
When did you last live there? You would likely be able to avoid capital gains on a sale under the 2 out of 5 rule.
I'm still living there now. Have been for 10 years. Converting it to a rental while I live outside the US.
So you would not pay any gains on the sale unless you have over $500k (married filing jointly)
 
2) do not maximize 401k / IRA plans - I look back on them and almost think it's almost a scam. Why? You do not know the tax rate when you need those funds. And your money is not liquid until you hit age >59, and more likely age 65 or so. In theory you will make less at age 65 when pulling it out than you will in your working years. But what if the tax rate doubles when you take it out? Or you need it earlier? Or the govt changes the rules? It's tied up as part of the system. And you don't control it Do however put in the max for your corporate match. That's free money. Take the free money.
Disagree strongly here. There are a few ways to access your money earlier and, if you do it right, you could end up never paying taxes on these funds.

Agree with D_P here. I think the "max your 401K at all costs" mantra has toned down a bit, and probably for good reason. But I sure don't think it's a scam or you shouldn't strive to do it if you can fill in the other buckets appropriate for your income and tax bracket.

Not sure what you mean by "more likely age 65 or so", but between Rule of 55 and 72T you can get to those funds earlier than 59 1/2 if you retire early and need access. More importantly, many people can take advantage of lower earnings years once you retire to roll 401K to a Roth while at lower tax brackets, paying little to no taxes on that money ever.

The tax brackets thing is a legit unknown, of course. As is "the gov't changes the rules", but that part would apply to every single savings and income vehicle.

The rest of your list, @Brunell4MVP - good stuff, appreciate you taking the time to post it.
 
Agree with D_P here. I think the "max your 401K at all costs" mantra has toned down a bit, and probably for good reason. But I sure don't think it's a scam or you shouldn't strive to do it if you can fill in the other buckets appropriate for your income and tax bracket.
I do think it makes sense to max the Roth IRA before 401k when able.

I recently did some analysis on my side and decided 24% marginal is worth the gamble, so we're going back towards the max.
 
not top 1%, but maybe top 3%.
Top 1% is about 10.5M net worth, top 5% is 3.8M net worth. If you have ~7M why in the world are you worried about medical insurance cost? Pay it out of your petty cash box.
I was going to include in my response “unless you’re a multimillionaire who is in the top tax bracket or two now and have enough assets to still be there in retirement” caveat.
 
Great list above. I agree with pretty much everything said - but I’m going to strongly agree with one, and strongly disagree with another.

Disagree - #2. As others have said, if properly constructed/managed, a traditional 401k or IRA can be a great tool - and potentially can end up having money never taxed. If f my wife and I have margin between income and expenses, why not lower our effective tax rate (even lower us into the next lower marginal rate) and allow for tax free growth - at least to the point where we can fill up the standard deduction and lower tax brackets. As even if the marginal rates are higher in retirement, I expect our taxable income to be lower.

Agree - permanent life insurance. I know it was stated specifically for universal life, but I’ll broaden that to any permanent life coverage. Just like the 401k idea above, if set up correctly it’s a great tool. In my working years it’s a replacement if my income to my spouse. Afterwards it’s a potential bump in retirement savings to a surviving spouse (assuming both have a policy). After that, should we both live long lives the cash value in our 90s is huge, should we need to tap into it - and if not it’s a no strings attached, tax free transfer to our child. That, conceptually, frees up our other assets to be used for what they were designed for - our retirement.
 
1) buy a house earlier, and pay it off fast. The latter part is not what many experts will tell you. They'll say spread those payments as long as possible and invest your extra instead. And we have a low interest rate of 2.75%. But the freedom of mind for having a paid off house is enormous when it comes to retirement and making decisions later in life. If you happen to pay it off fast, you can then buy rental properties or rent your own place or make more investments. The freedom of no mortgage is more important than the few extra bucks you might make investing You know who tells you to not pay it off? Investment professionals that make money off your investments. Get a 30 year loan to keep the stress down, and try to pay 10% more per payment. Amazing how much you will save in interest. And your investment is in an appreciating asset.

2) do not maximize 401k / IRA plans - I look back on them and almost think it's almost a scam. Why? You do not know the tax rate when you need those funds. And your money is not liquid until you hit age >59, and more likely age 65 or so. In theory you will make less at age 65 when pulling it out than you will in your working years. But what if the tax rate doubles when you take it out? Or you need it earlier? Or the govt changes the rules? It's tied up as part of the system. And you don't control it Do however put in the max for your corporate match. That's free money. Take the free money.
Overall, great post. I do want to add to the first two though.

1) As a mortgage broker and someone who has been in banking/financial services for well over 20 years, one thing that I have long ago realized and accepted that was crucial for me to be able to provide excellent professional guidance for my clients is this: There are very, very, very few 'always, never' type answers in deciding what to do with financial matters. There are reasons for this which include different people having different variables with different wants and needs. But a huge part of personal finance that many just ignore is that it is heavily psychological. It often comes down to risk and sleeping well at night. For some, being conservative will actually be harmful to their peace of mind because they are naturally more aggressive. For others, they are on the other side and want to minimize risk as much as possible. Paying off a mortgage as soon as possible when you have a rate under 3% is certainly on the conservative side- and there is absolutely nothing wrong with that. Just as much as using the extremely low cost of leveraging the home to increase cash flow and increase assets elsewhere.

2) This is largely why it is important to mix your retirement funds with ROTH and traditional to provide more flexibility. Also, if you are able to with your insurance then getting and maxing out an HSA is by far your first priority above 401k/IRA contributions. HSA basically has all the benefits of the retirement funds with none of the drawbacks.
 
7. If possible, never sell your houses - If you are forced to move, rent your current house and save up for the downpayment on the next. Most of our super wealthy friends have 5-10 homes. They have the dump they started in, then a few move up homes. And they are pulling in $4-8K per house (big metro area). And a few are paid off, so it's pure income other than the taxes and insurance. One of my buddies make $34K/month on rentals where he has paid off the homes. That is living my friends. We sold our $125K TH 25 years ago because we needed the $20K down for the next house. That TH is now worth $680K. What a dumb decision, all to get a smaller payment on the next house. Find a way to hold rather than sell your real estate assets.
Also on this. This actually is great advice but again there are very few 'always, never' in personal finance. An example here would be me as we were recently looking to buy another home. I very much wanted to keep our current home to rent. However, my wife was very much against it. The big reason for this was my health. I have a bad back (among other issues) that makes it extremely hard to deal with even the most minor of household day to day lives at times (like right now). As a landlord, I would then have to pay someone to do whatever needed to be done on the house at all times which can be very expensive. It was something I still wanted to do because at my calculations of what rental comps were for our house, we would have well enough extra cash flow to use to do exactly that but going back to what I was saying before about peace of mind.... my wife would have no peace of mind about it. No matter how something can benefit you, if you can't sleep at night then it is not worth it.
 
7. If possible, never sell your houses - If you are forced to move, rent your current house and save up for the downpayment on the next. Most of our super wealthy friends have 5-10 homes. They have the dump they started in, then a few move up homes. And they are pulling in $4-8K per house (big metro area). And a few are paid off, so it's pure income other than the taxes and insurance. One of my buddies make $34K/month on rentals where he has paid off the homes. That is living my friends. We sold our $125K TH 25 years ago because we needed the $20K down for the next house. That TH is now worth $680K. What a dumb decision, all to get a smaller payment on the next house. Find a way to hold rather than sell your real estate assets.
Also on this. This actually is great advice but again there are very few 'always, never' in personal finance. An example here would be me as we were recently looking to buy another home. I very much wanted to keep our current home to rent. However, my wife was very much against it. The big reason for this was my health. I have a bad back (among other issues) that makes it extremely hard to deal with even the most minor of household day to day lives at times (like right now). As a landlord, I would then have to pay someone to do whatever needed to be done on the house at all times which can be very expensive. It was something I still wanted to do because at my calculations of what rental comps were for our house, we would have well enough extra cash flow to use to do exactly that but going back to what I was saying before about peace of mind.... my wife would have no peace of mind about it. No matter how something can benefit you, if you can't sleep at night then it is not worth it.
It was probably a financial mistake to sell my townhome after renting it for a few years but getting that equity liquid before having a kid and doing an extension was a great piece of mind.
 
Agree with D_P here. I think the "max your 401K at all costs" mantra has toned down a bit, and probably for good reason. But I sure don't think it's a scam or you shouldn't strive to do it if you can fill in the other buckets appropriate for your income and tax bracket

:2cents: Traditional vs Roth is a major consideration in 401ks. We’ve discussed it before, but I’m happily doing 62% Roth contributions currently, 22% marginal tax rate. If rates stay where they are (Congress might make that happen), I don’t see us ever being below this bracket - whether that’s due to withdrawing from the traditional accounts or social security.
 
401K is safe from bankruptcy. Almost everyone is one bad medical event from financial disaster. I had a thing that insurance fought and didn't cover that was 80k. I ended up not having to pay it, but it sure opened my eyes. In my state they can take your house, but not your 401k in a bankruptcy.
 
I'm trying to frame my "buckets" to give me the most options when I enter "De-accumulation" phase. Traditional, Roth, HSA, brokerage, cash equivalents, & i-bonds all play a role in how I will control my current and future tax bills as well as opportunities to access cash before 59.5 should I chose/forced into an early retirement. I'm a spreadsheet geek, so trying to balance where future expenses will be funded from is kinda fun.
 
401K is safe from bankruptcy. Almost everyone is one bad medical event from financial disaster. I had a thing that insurance fought and didn't cover that was 80k. I ended up not having to pay it, but it sure opened my eyes. In my state they can take your house, but not your 401k in a bankruptcy.

Also in a similar vein - 401k isn’t counted as an “asset” when going through the FASFA process to determine financial aid status for college, while a traditional brokerage account is. If saving “for the future”, once your financial basics are covered (emergency fund, good insurance), not much beats a 401k/ira/roth.
 
I'm trying to frame my "buckets" to give me the most options when I enter "De-accumulation" phase. Traditional, Roth, HSA, brokerage, cash equivalents, & i-bonds all play a role in how I will control my current and future tax bills as well as opportunities to access cash before 59.5 should I chose/forced into an early retirement. I'm a spreadsheet geek, so trying to balance where future expenses will be funded from is kinda fun
:yes: although I’ve been considering I bonds as cash equivalents. Other than not being subject to state tax, is there a reason to make a distinction?
 
I'm trying to frame my "buckets" to give me the most options when I enter "De-accumulation" phase. Traditional, Roth, HSA, brokerage, cash equivalents, & i-bonds all play a role in how I will control my current and future tax bills as well as opportunities to access cash before 59.5 should I chose/forced into an early retirement. I'm a spreadsheet geek, so trying to balance where future expenses will be funded from is kinda fun
:yes: although I’ve been considering I bonds as cash equivalents. Other than not being subject to state tax, is there a reason to make a distinction?
I get taxed on HYSA/dividends every year - i Bonds I get taxed when I sell. Up to 30 years of tax deferral is nice.
 
I'm trying to frame my "buckets" to give me the most options when I enter "De-accumulation" phase. Traditional, Roth, HSA, brokerage, cash equivalents, & i-bonds all play a role in how I will control my current and future tax bills as well as opportunities to access cash before 59.5 should I chose/forced into an early retirement. I'm a spreadsheet geek, so trying to balance where future expenses will be funded from is kinda fun
:yes: although I’ve been considering I bonds as cash equivalents. Other than not being subject to state tax, is there a reason to make a distinction?
I get taxed on HYSA/dividends every year - i Bonds I get taxed when I sell. Up to 30 years of tax deferral is nice.
That’s a nice benefit if you expect to have a lower marginal tax rate when you sell the I bonds. I don’t expect to be lower, so I’m not seeing the benefit of the deferred tax. But for many that makes a lot of sense.
 
I'm trying to frame my "buckets" to give me the most options when I enter "De-accumulation" phase. Traditional, Roth, HSA, brokerage, cash equivalents, & i-bonds all play a role in how I will control my current and future tax bills as well as opportunities to access cash before 59.5 should I chose/forced into an early retirement. I'm a spreadsheet geek, so trying to balance where future expenses will be funded from is kinda fun
:yes: although I’ve been considering I bonds as cash equivalents. Other than not being subject to state tax, is there a reason to make a distinction?
I get taxed on HYSA/dividends every year - i Bonds I get taxed when I sell. Up to 30 years of tax deferral is nice.
That’s a nice benefit if you expect to have a lower marginal tax rate when you sell the I bonds. I don’t expect to be lower, so I’m not seeing the benefit of the deferred tax. But for many that makes a lot of sense.
My initial thought is if I cash them out before SS and RMDs, but after I stop working, my tax rate should be lower. I think I'll have a lot of control of my tax brackets in my 60s.
 
I'm trying to frame my "buckets" to give me the most options when I enter "De-accumulation" phase. Traditional, Roth, HSA, brokerage, cash equivalents, & i-bonds all play a role in how I will control my current and future tax bills as well as opportunities to access cash before 59.5 should I chose/forced into an early retirement. I'm a spreadsheet geek, so trying to balance where future expenses will be funded from is kinda fun
:yes: although I’ve been considering I bonds as cash equivalents. Other than not being subject to state tax, is there a reason to make a distinction?
I get taxed on HYSA/dividends every year - i Bonds I get taxed when I sell. Up to 30 years of tax deferral is nice.
That’s a nice benefit if you expect to have a lower marginal tax rate when you sell the I bonds. I don’t expect to be lower, so I’m not seeing the benefit of the deferred tax. But for many that makes a lot of sense.
My initial thought is if I cash them out before SS and RMDs, but after I stop working, my tax rate should be lower. I think I'll have a lot of control of my tax brackets in my 60s.
Yeah, that’s when I plan to use my traditional IRA. That should be at around $1M when I’m 60. Using that before we claim SS, so 10ish years. Not a bad problem but one requiring planning
 
I'm trying to frame my "buckets" to give me the most options when I enter "De-accumulation" phase. Traditional, Roth, HSA, brokerage, cash equivalents, & i-bonds all play a role in how I will control my current and future tax bills as well as opportunities to access cash before 59.5 should I chose/forced into an early retirement. I'm a spreadsheet geek, so trying to balance where future expenses will be funded from is kinda fun
:yes: although I’ve been considering I bonds as cash equivalents. Other than not being subject to state tax, is there a reason to make a distinction?
I get taxed on HYSA/dividends every year - i Bonds I get taxed when I sell. Up to 30 years of tax deferral is nice.
do i bonds count for fafsa purposes?
 
I'm trying to frame my "buckets" to give me the most options when I enter "De-accumulation" phase. Traditional, Roth, HSA, brokerage, cash equivalents, & i-bonds all play a role in how I will control my current and future tax bills as well as opportunities to access cash before 59.5 should I chose/forced into an early retirement. I'm a spreadsheet geek, so trying to balance where future expenses will be funded from is kinda fun
:yes: although I’ve been considering I bonds as cash equivalents. Other than not being subject to state tax, is there a reason to make a distinction?
I get taxed on HYSA/dividends every year - i Bonds I get taxed when I sell. Up to 30 years of tax deferral is nice.
do i bonds count for fafsa purposes?

Yes
 

Why wouldn’t it? It’s just cash.
Plus you might not pay taxes if used for college.

You can take the tax exclusion if you meet all of these conditions:

  • You were 24 years old or older before the bonds were issued.
  • Your modified adjusted gross income is less than the cut-off amount that the IRS sets for the year in which you want to take the exclusion. The cut-off amount may change each year. You can find the current cut-off amount on IRS Form 8815.
  • You cash the qualifying savings bonds in the same tax year for which you are claiming the exclusion.
  • You paid qualified higher education expenses to an eligible institution that same tax year. (The instructions that come with IRS Form 8815 explain both "qualified expenses" and "eligible institution." They also tell you what records you must keep.)
  • The expenses were for yourself, your spouse, or someone you list as a dependent on your federal income tax return.
  • You file your IRS tax return with any status EXCEPT married filing separately.
 
Just wanted to get some opinions on this:

We always take a trip in January and use our credit card points to pay for the flights which usually covers it.
Typically what we do is book it through the ultimate rewards site through chase as opposed to converting the points to cash and paying it that way.
I do notice the ultimate rewards site is not the most user friendly site and was wondering if there are any advantages with doing it this way vs getting the cash deposited in my checking account (or credit card) and paying for it that way?
 
Just wanted to get some opinions on this:

We always take a trip in January and use our credit card points to pay for the flights which usually covers it.
Typically what we do is book it through the ultimate rewards site through chase as opposed to converting the points to cash and paying it that way.
I do notice the ultimate rewards site is not the most user friendly site and was wondering if there are any advantages with doing it this way vs getting the cash deposited in my checking account (or credit card) and paying for it that way?

Neither is optimal. Find the flight(s) you want, and look at how many miles it would take on that airline to book, and transfer the miles. Next level is to instead find a partner airline (likewith the highest transfer ratio that offers that same flight, transfer your points to that airline. Book flights.

Here are a couple of other articles on the topic

How (and why) you should earn transferable credit card points in 2024

How to transfer credit card rewards points to partner programs

Full disclaimer - I just entered the transferable points world this year for the first time with both the Amex Platinum and the Chase Sapphire Preferred. In just a couple of months I've built up almost 90K Amex MR points and 96K Chase UR points thanks to the sign up bonuses, but I haven't actually tried to use any of them yet (other than using 1 MR point at Amazon to get $75 off an order). So while transferring the points to an airline sounds like better value most of the time than their own portals or cash, that next step of using partner airlines instead does seem like it could get complicated. But they make it sound easy!
 
Just wanted to get some opinions on this:

We always take a trip in January and use our credit card points to pay for the flights which usually covers it.
Typically what we do is book it through the ultimate rewards site through chase as opposed to converting the points to cash and paying it that way.
I do notice the ultimate rewards site is not the most user friendly site and was wondering if there are any advantages with doing it this way vs getting the cash deposited in my checking account (or credit card) and paying for it that way?

Neither is optimal. Find the flight(s) you want, and look at how many miles it would take on that airline to book, and transfer the miles. Next level is to instead find a partner airline (likewith the highest transfer ratio that offers that same flight, transfer your points to that airline. Book flights.

Here are a couple of other articles on the topic

How (and why) you should earn transferable credit card points in 2024

How to transfer credit card rewards points to partner programs

Full disclaimer - I just entered the transferable points world this year for the first time with both the Amex Platinum and the Chase Sapphire Preferred. In just a couple of months I've built up almost 90K Amex MR points and 96K Chase UR points thanks to the sign up bonuses, but I haven't actually tried to use any of them yet (other than using 1 MR point at Amazon to get $75 off an order). So while transferring the points to an airline sounds like better value most of the time than their own portals or cash, that next step of using partner airlines instead does seem like it could get complicated. But they make it sound easy!
Agree with all of this. In order of "best value" is almost always:

1. Transfer to a partner airline with a fixed rate flight chart (ETA: when I have done this, I have called the partner airline first and placed a 24-hour hold on the redemption, then transferred points after confirming it works, then calling again to confirm they got the points)
2. Transfer to the airline you're flying
3. Use their travel portal (I think you get a higher cpp than you do taking cash back usually but this can vary by card)
4. Cash back

Sometimes, depending on where you are going and what you like, you may find it is better $$ for you overall to transfer Chase UR points to Hyatt, book a nice hotel(s) the whole time, and pay for a flight. But that's heavily dependent on which hotels, which flights, how far out, etc.
 
Just wanted to get some opinions on this:

We always take a trip in January and use our credit card points to pay for the flights which usually covers it.
Typically what we do is book it through the ultimate rewards site through chase as opposed to converting the points to cash and paying it that way.
I do notice the ultimate rewards site is not the most user friendly site and was wondering if there are any advantages with doing it this way vs getting the cash deposited in my checking account (or credit card) and paying for it that way?
You get a 25% point value increase when booking through the portal. The thing you want to consider is that the portal doesn't always have the best flight price. I've noticed this when united has a significant drop in price for just a day (see this when tracking via Google flights), but the portal doesn't reflect that drop.
 
Just wanted to get some opinions on this:

We always take a trip in January and use our credit card points to pay for the flights which usually covers it.
Typically what we do is book it through the ultimate rewards site through chase as opposed to converting the points to cash and paying it that way.
I do notice the ultimate rewards site is not the most user friendly site and was wondering if there are any advantages with doing it this way vs getting the cash deposited in my checking account (or credit card) and paying for it that way?
You get a 25% point value increase when booking through the portal. The thing you want to consider is that the portal doesn't always have the best flight price. I've noticed this when united has a significant drop in price for just a day (see this when tracking via Google flights), but the portal doesn't reflect that drop.
Sometimes it works on the way back up, as well - you can still capture a low price. I've had luck with finding cheap fares (Scott's cheap fares or similar) and then booking through the portal. Paying with cheap points is muy bueno.
 
So I have freedom unlimited. I don't know if that card allows me to transfer points to travel partners?

Ahh, in that case it doesn't look like it, unless you have one of their other cards that does.

"Alone, the Freedom Unlimited is a true cash-back card and doesn't allow you to transfer your rewards to travel partners.
However, if you also have the Chase Sapphire Preferred Card, the Chase Sapphire Reserve or the Ink Business Preferred Credit Card, you can combine your rewards and unlock Chase's full list of 14 hotel and airline partners."


If that's the case, you'd probably just want to compare the cash price of the flights booked directly with what it would cost you in the portal (factoring in the 5% cashback bonus you get for booking in the portal).
 
Just wanted to get some opinions on this:

We always take a trip in January and use our credit card points to pay for the flights which usually covers it.
Typically what we do is book it through the ultimate rewards site through chase as opposed to converting the points to cash and paying it that way.
I do notice the ultimate rewards site is not the most user friendly site and was wondering if there are any advantages with doing it this way vs getting the cash deposited in my checking account (or credit card) and paying for it that way?
You get a 25% point value increase when booking through the portal. The thing you want to consider is that the portal doesn't always have the best flight price. I've noticed this when united has a significant drop in price for just a day (see this when tracking via Google flights), but the portal doesn't reflect that drop.

Another thing to think about when booking thru a portal is they are basically a travel agent. If you have any problems or need to make changes, you’re usually going to be dealing with them instead of the airline or hotel. That can be good or bad depending on the situation.

Edit: Also, a lot of portal bookings say they are non-refundable so keep that in mind. It doesn’t mean you can’t ask for a refund if your plans change but you may be at their mercy if they will grant one or not.
 
Just wanted to get some opinions on this:

We always take a trip in January and use our credit card points to pay for the flights which usually covers it.
Typically what we do is book it through the ultimate rewards site through chase as opposed to converting the points to cash and paying it that way.
I do notice the ultimate rewards site is not the most user friendly site and was wondering if there are any advantages with doing it this way vs getting the cash deposited in my checking account (or credit card) and paying for it that way?
You get a 25% point value increase when booking through the portal. The thing you want to consider is that the portal doesn't always have the best flight price. I've noticed this when united has a significant drop in price for just a day (see this when tracking via Google flights), but the portal doesn't reflect that drop.

Another thing to think about when booking thru a portal is they are basically a travel agent. If you have any problems or need to make changes, you’re usually going to be dealing with them instead of the airline or hotel. That can be good or bad depending on the situation.

Edit: Also, a lot of portal bookings say they are non-refundable so keep that in mind. It doesn’t mean you can’t ask for a refund if your plans change but you may be at their mercy if they will grant one or not.
Another excellent point.

I hate the portals for this reason. I do my very best to always book directly, as I have found I get much better service. Now, if I could book all my personal travel through Amex GBT I'd do that too, but not an option LOL.
 
For you noobs, 10x Travel is a good FB group to join. They have a course you can read through that gives you a solid foundation on how this all works.

It still takes work to really maximize points usage, but once you do it's worth it, I think. Flying business class to Madrid in March and back for only 68K in points round trip, as an example. That's basically one sign-up bonus.
 
Random thoughts of an older guy that has learned from some small errors ...background ... we are fairly fortunate. not top 1%, but maybe top 3%. Put 2 kids through college. Mid-50s and could retire but will keep working for another 5-10 years mostly to cover the cost of medical insurance since we are self-employed and we'd be bored if we didn't have any work to do.

Here's some things I wish I had done different ... and I'll caveat I am not an investment professional. Just feel like we as little people get duped into a few things.

1) buy a house earlier, and pay it off fast. The latter part is not what many experts will tell you. They'll say spread those payments as long as possible and invest your extra instead. And we have a low interest rate of 2.75%. But the freedom of mind for having a paid off house is enormous when it comes to retirement and making decisions later in life. If you happen to pay it off fast, you can then buy rental properties or rent your own place or make more investments. The freedom of no mortgage is more important than the few extra bucks you might make investing You know who tells you to not pay it off? Investment professionals that make money off your investments. Get a 30 year loan to keep the stress down, and try to pay 10% more per payment. Amazing how much you will save in interest. And your investment is in an appreciating asset.

2) do not maximize 401k / IRA plans - I look back on them and almost think it's almost a scam. Why? You do not know the tax rate when you need those funds. And your money is not liquid until you hit age >59, and more likely age 65 or so. In theory you will make less at age 65 when pulling it out than you will in your working years. But what if the tax rate doubles when you take it out? Or you need it earlier? Or the govt changes the rules? It's tied up as part of the system. And you don't control it Do however put in the max for your corporate match. That's free money. Take the free money.

3. Use 529 plans - Why these but not the 401k? Because you are going to use the 529 much earlier in life. And you are gonna pay for college if you have kids so get it out of the way ASAP. It will really help them get off your payroll if they don't have college debt. It's an ease of mind thing to know it's paid for early on.

4. Do not use an investment advisor unless you have more than the inheritance tax threshold. Why? Even if your professional is cheap at like $5k/year ... amortize that over 30 years at the S&P growth rate of 8%. It's almost $700,000 you've paid for that "advice" which is really just an investment mix in one of their standard portfolios. Now once you hit the inheritance threshold, you need legal advice to create trusts and other tax avoidance strategies. That is worth paying for to help the next generation. But $700K in costs for the potential to make 1-2% more in the advisors "investment mix" is not worth the risk.

5. Put all your stock investments into the S%P 500 index fund or a mix of the S&P large, mid, and small caps - Why? It's a great return in the long run. And you do not know more than everyone else. And you certainly don't know more than large firms helping the super wealthy with hundreds of computers figuring it out. Warren Buffett also backs this strategy. If you want play money for crypto or a few individual stocks for fun ... hey live a little. But you are not going to outsmart the system. Just ride the wave that is the US Economy.

6. As odd as it sounds since it's a bad investment, I wish we had signed up for a universal life insurance plan. We did term insurance. Sure it's cheap. It will also go away in a couple of years, or get prohibitively expensive. The ULI would have been better as I look back. It has really helped a few friends that lost spouses. At worst someone is getting a lump sum payout at a low savings rate.

7. If possible, never sell your houses - If you are forced to move, rent your current house and save up for the downpayment on the next. Most of our super wealthy friends have 5-10 homes. They have the dump they started in, then a few move up homes. And they are pulling in $4-8K per house (big metro area). And a few are paid off, so it's pure income other than the taxes and insurance. One of my buddies make $34K/month on rentals where he has paid off the homes. That is living my friends. We sold our $125K TH 25 years ago because we needed the $20K down for the next house. That TH is now worth $680K. What a dumb decision, all to get a smaller payment on the next house. Find a way to hold rather than sell your real estate assets.

8. Teach your kids a budget - our kids are smart and thifty and luckily doing great. they also were not worldly when it came to money. Like what groceries, cars, houses, etc cost Or even what we paid for. Like they had no idea what home or car insurance was. They have learned quickly since getting out of college.. Sit down with them and show them your budget at like ages 11-14. My wife did not want them to know what we made. It's important they understand so they appreciate the value of a good job

9. Earnings potential is so important - When I met my wife I was doing just fine in computer jobs. She was in sales. If you want to make money you need a job that has high potential earnings. You can be very comfy in a normal 8-6 job. Which keeps you up with the Joneses. You want to exceed the standard? It's not an 8-6 job. It a full time, 24 hour, work your *** job and earn commissions or stock incentives or run your own business job. It's not for everyone. But limited income = limited wealth.

I'm sure there are more. But these are the ones I've been stewing through as I look back on my first 50 years.
1 - I tend to agree and don't regret paying off my house as fast as I could despite it only being 3% ish interest.
2 - Disagree. Especially in later years I can't find enough places to plow money into tax sheltered accounts. I'm going to have a bunch of cash once I retire that's going to have to be invested non-tax sheltered which sucks. I am also doing regular 401k instead of Roth 401k right now because I'm at a very high tax bracket. Will roll over to Roth after retirement at a much lower tax bracket. Roth 401K for early in your career when you are in a low tax bracket.
3 - No kids. Too late for grandkids.
4 - Agree 100%. Simpler is better and simple anyone can do.
5 - Or a total market index fund for more diversification closer to retirement. 10-20% into total international market index for even more diversification.
6 - Not for me.
7 - Disagree. Too situational. I don't want to live where I currently own a home and I got 300K extra by selling and buying where I do want to live in a much lower cost of living area. Also, I have no interest in being a land lord, no thanks.
8 - Agree.
9 - Agree.
 
You guys might as well be speaking Chinese
HAHA

I do find that this is one hobby (the points stuff and churning) that people HEAVILY gatekeep and make very mystical. At the end of the day, simplifying it has made for some great vacations at great value and relatively low effort.

Travel partnerships - most applicable for airlines: All the airlines have these deals with each other. They give their own mileage members access to other airlines' flights. Often international airlines have a fixed rate, like "30k miles for any first class ticket from Europe to North America with airline x" (that's how we went to Japan - we put points from our Chase UR account out to Virgin U.K. airline and booked a Delta One first class cabin from U.S. To Japan. Virgin and Delta have some deal that allows x cabin for y miles between these two regions (whereas putting them to Delta miles would have exposed us to their demand-based pricing, where an expensive seat costs more miles also). At a more basic level, airlines have alliances that recognize status too - for all the "OneWorld" members, my American Airlines top tier status gets me all the highest benefits on those other airlines as well.

Transfer partners - this is the group of companies you can send your credit card points to. For example, Chase has like 8 airlines, 3 hotel chains, maybe a car company or two, etc. You can send your Chase Points to your account at those partners. The consistent highest and best use I have found for Chase UR points is not to use them for cash back or in Chase's travel portal, but to send them to my Hyatt account and book hotels with them.

Travel portal - most CC companies have a portal where they have a basic travel agency and you can spend your points there, generally for 1 cent per point or 1.5 cents per point. I typically fidn the prices are poor and the service is mediocre. I generally advise you avoid.

There are some other details to earning points that can range from extremely simple (we have a Chase Sapphire and use it for everything!) to moderately complex (A - we sign up for a new card whenever we have a bigger string of purchases to get a big sign up bonus amount of points or B - we have a couple cards that earn more than 1x/dollar spent , like the Hyatt card to use at Hyatt hotels, or the whatever card for gas as a bonus category or the like) to the extremely complicated (a different card for every type of spend, and rotating sign up bonuses, and hunting targeted offers that have bigger bonuses, and "manufacturing" spend that is in a grey area of whether it's allowed or not. One example of that was buying gold dollars, depositing them into your bank account, and continuing to do it over and over to pay for the gold dollar coins...)
 
If you have good credit, can keep a spreadsheet, and are willing to do a tad bit of homework credit card rewards are an easy 20-40k a year extra. If you can find the right connections and not be a **** can double that. If you value things like first class seats and five star hotels at their face value, then it just goes up from there.
 
For you noobs, 10x Travel is a good FB group to join. They have a course you can read through that gives you a solid foundation on how this all works.

It still takes work to really maximize points usage, but once you do it's worth it, I think. Flying business class to Madrid in March and back for only 68K in points round trip, as an example. That's basically one sign-up bonus.

i sent this to the Mrs last month after signing up for chase sapphire preferred.

We have always been cash back, but with sign up bonuses there is no reason not to play their game. As long as we sign up for full automatic bill payment, i don't see any downside.

I think our goal should be travel rewards. While cash back is nice, all that would do is go back to our account and we would never see/use the actual benefits. We all want to travel places, but it's expensive so getting rewards can help reduce/eliminate that.

There are several travel programs. but the industry recognized best option is chase. it offers the most flexibility and good returns. they allow transferring within household, but also to airline partners to use as their own reward miles.

We took step one getting chase sapphire reserve several weeks ago. Credit cards have a rule of not allowing more than 5 new accounts in 24 months. And they don't like it when you open accounts with less than 3 months between each account.

With Chase, the next cards to get for individuals are chase freedom flex and chase freedom unlimited. They offer mileage rewards which I won't get into, but they offer 20k signup miles with marginal spending. Doing the 3 months between offers (since I was primary for sapphire) means opening one up in september and December. With their rewards, plus whatever from spending, and we will have well over 100k miles (which is basically $1250 in travel rewards) by the end of the year.

Now, going back to transferring within household i mentioned earlier. Chase offers a credit card for businesses that is incredible. They follow the same rules of 3 month spacing and 5 in 24 months, but... it's tied to the business not the person. So, once your business has some profit and time (probably in 3 months), you can sign up for the Chase Ink unlimited business card (75k rewards after spending 6k in 3 months.). that's some spending, so we will need to be targeting that. then 3 months later sign up for chase ink business cash which has same rewards and same spending.

We could open up your own chase individual cards, but the business cards offer more rewards and at some point we would be overwhelmed with confusion. If not already there.

What this means is that if we execute, we can have 60+20+20+75+75=250k in reward miles by the end of the year. if we book through chase, and their 25% multiplier, that is $3,125 going towards air/hotel on a future trip.

If we transfer to an airline/hotel the rewards can be even 2x-3x if we put in the effort and are flexible.
 
For you noobs, 10x Travel is a good FB group to join. They have a course you can read through that gives you a solid foundation on how this all works.

It still takes work to really maximize points usage, but once you do it's worth it, I think. Flying business class to Madrid in March and back for only 68K in points round trip, as an example. That's basically one sign-up bonus.
Holy crap!!

That website has an incredible amount of free resources. I'm going to be busy for the next month.
 
I think I’m taking our oldest to Cleveland in March to see the rock and roll HoF. We’ll fly instead of driving 10 hours.
What’s the best deal going for tickets? We’ll want to fly from Huntsville to Cleveland.
 

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