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Personal Finance Advice and Education! (3 Viewers)

Awesome thread; couple questions for the room:

My wife is 13 years younger. We fully fund my Roth. Should we also fund hers knowing that when she turns 59 we will already be withdrawing from my 401k no penalty for several years?

Also, saw someone post about 529 tax breaks. Do you have to live in the state where your 529 is to be eligible? We are in FL, but our 529 is in VA. Thanks
For a wife significantly younger, I would think the following would be important:

-life insurance for you

-what will she do when you retire (if she is working now)?

-is she involved in the family finances? if not, I would get her involved as she is highly likely to outlive you (82% more likely per the life expectancy calculator I use, assuming you are 50 now)

 
FWIW Millionaire Next Door is available to borrow for free if you have a Kindle and Amazon Prime. Thanks to everyone who recommended it :thumbup:

 
I earn a ton of loot but I'm broke. Can I hire Dentist to come and live with me for a while, like when Chris comes to live with the fat people in the first 3 months of training in Extreme Makeover Weight Loss Edition?

 
So my wife is becoming a partner this month. I know we will need to file quarterly taxes now but is there anything else I should be aware of?

I plan to meet with our accountant later this month.

Thanks.
Your wife is a lesbian?
You know I was going to add the word work. "Partner at work " but thought oh they will know what I mean. I guess not everyone.

So anyone have any advise? Has to be some other people that are in partnerships.

 
wilked said:
JackReacher said:
Awesome thread; couple questions for the room:

My wife is 13 years younger. We fully fund my Roth. Should we also fund hers knowing that when she turns 59 we will already be withdrawing from my 401k no penalty for several years?

Also, saw someone post about 529 tax breaks. Do you have to live in the state where your 529 is to be eligible? We are in FL, but our 529 is in VA. Thanks
For a wife significantly younger, I would think the following would be important:-life insurance for you

-what will she do when you retire (if she is working now)?

-is she involved in the family finances? if not, I would get her involved as she is highly likely to outlive you (82% more likely per the life expectancy calculator I use, assuming you are 50 now)
I'm 44, she's 31. She has her own small business. We do all of the finances together; basically educated by watching Suze Orman. I have a large life insurance policy from work, but definitely need to start thinking now about having insurance in place for when I am done working. Our goal is for me to retire at 60. She wants to work until she's 55, so for 8 years after I retire. When I retire, we will use her work earnings, start taking my pension and use the Roth to bridge gap until when we start taking from the 401K. Sound plan?

 
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Wooderson said:
eoMMan said:
Wooderson said:
So my wife is becoming a partner this month. I know we will need to file quarterly taxes now but is there anything else I should be aware of?

I plan to meet with our accountant later this month.

Thanks.
Your wife is a lesbian?
You know I was going to add the word work. "Partner at work " but thought oh they will know what I mean. I guess not everyone. So anyone have any advise? Has to be some other people that are in partnerships.
Just joking, bro...

She'll get a schedule k-1 that will show her portion of the partnerships profit/loss. This will then get reported on your joint personal tax. How much extra that she/you need to pay in via tax estimates depends on how well (or bad) the partnership does. I'm assuming she'll have a decent idea of this as the year progresses. You can then give this projection to your accountant and they will calculate your estimates accordingly.

 
wilked said:
JackReacher said:
Awesome thread; couple questions for the room:

My wife is 13 years younger. We fully fund my Roth. Should we also fund hers knowing that when she turns 59 we will already be withdrawing from my 401k no penalty for several years?

Also, saw someone post about 529 tax breaks. Do you have to live in the state where your 529 is to be eligible? We are in FL, but our 529 is in VA. Thanks
For a wife significantly younger, I would think the following would be important:-life insurance for you

-what will she do when you retire (if she is working now)?

-is she involved in the family finances? if not, I would get her involved as she is highly likely to outlive you (82% more likely per the life expectancy calculator I use, assuming you are 50 now)
I'm 44, she's 31. She has her own small business. We do all of the finances together; basically educated by watching Suze Orman. I have a large life insurance policy from work, but definitely need to start thinking now about having insurance in place for when I am done working. Our goal is for me to retire at 60. She wants to work until she's 55, so for 8 years after I retire.When I retire, we will use her work earnings, start taking my pension and use the Roth to bridge gap until when we start taking from the 401K. Sound plan?
I have no way of telling if it is a good plan from this. If you want a review you will have to post a whole lot more, including assets, debt, pension size, salaries, expenses. I mean it sounds like a fine plan in general but it's the details that will make or break you

 
We have discover now and would keep it for the 5%, but I'd like more on everything.

Just reluctant to apply for another card (we only have 2)
So I applied for the card, got rejected. :lol: apparently when filling out the form I thought they were asking monthly salary when they were asking annual. They seemingly didn't bother to check our score.

Not real sure if I'll call and correct it.

 
Wooderson said:
eoMMan said:
Wooderson said:
So my wife is becoming a partner this month. I know we will need to file quarterly taxes now but is there anything else I should be aware of?

I plan to meet with our accountant later this month.

Thanks.
Your wife is a lesbian?
You know I was going to add the word work. "Partner at work " but thought oh they will know what I mean. I guess not everyone. So anyone have any advise? Has to be some other people that are in partnerships.
Just joking, bro...She'll get a schedule k-1 that will show her portion of the partnerships profit/loss. This will then get reported on your joint personal tax. How much extra that she/you need to pay in via tax estimates depends on how well (or bad) the partnership does. I'm assuming she'll have a decent idea of this as the year progresses. You can then give this projection to your accountant and they will calculate your estimates accordingly.
No worries.

So we still only pay taxes once a year ? But she will get four k-1s?

For some reason I was thinking we paid in 4 times during the year and then in April we either pay more to settle up or they pay out any extra we may have put in.

Thanks

 
wilked said:
JackReacher said:
Awesome thread; couple questions for the room:

My wife is 13 years younger. We fully fund my Roth. Should we also fund hers knowing that when she turns 59 we will already be withdrawing from my 401k no penalty for several years?

Also, saw someone post about 529 tax breaks. Do you have to live in the state where your 529 is to be eligible? We are in FL, but our 529 is in VA. Thanks
For a wife significantly younger, I would think the following would be important:-life insurance for you

-what will she do when you retire (if she is working now)?

-is she involved in the family finances? if not, I would get her involved as she is highly likely to outlive you (82% more likely per the life expectancy calculator I use, assuming you are 50 now)
I'm 44, she's 31. She has her own small business. We do all of the finances together; basically educated by watching Suze Orman. I have a large life insurance policy from work, but definitely need to start thinking now about having insurance in place for when I am done working. Our goal is for me to retire at 60. She wants to work until she's 55, so for 8 years after I retire.When I retire, we will use her work earnings, start taking my pension and use the Roth to bridge gap until when we start taking from the 401K. Sound plan?
I have no way of telling if it is a good plan from this. If you want a review you will have to post a whole lot more, including assets, debt, pension size, salaries, expenses. I mean it sounds like a fine plan in general but it's the details that will make or break you
I will send a PM. Thanks GB
 
Wooderson said:
eoMMan said:
Wooderson said:
So my wife is becoming a partner this month. I know we will need to file quarterly taxes now but is there anything else I should be aware of?

I plan to meet with our accountant later this month.

Thanks.
Your wife is a lesbian?
You know I was going to add the word work. "Partner at work " but thought oh they will know what I mean. I guess not everyone. So anyone have any advise? Has to be some other people that are in partnerships.
Just joking, bro...She'll get a schedule k-1 that will show her portion of the partnerships profit/loss. This will then get reported on your joint personal tax. How much extra that she/you need to pay in via tax estimates depends on how well (or bad) the partnership does. I'm assuming she'll have a decent idea of this as the year progresses. You can then give this projection to your accountant and they will calculate your estimates accordingly.
No worries. So we still only pay taxes once a year ? But she will get four k-1s?

For some reason I was thinking we paid in 4 times during the year and then in April we either pay more to settle up or they pay out any extra we may have put in.

Thanks
You are correct in that you will file your normal 1040 return annually but the partnership will need to file their return first and then distribute the schedule k1s to the partners. There will just be one annual k1 for the partnership (under most circumstances).

Your last paragraph is correct. The IRS wants you to make 4 quarterly tax estimates to cover your tax liability (considering of course any other withholdings or tax payments). When you then file your 1040, you might need to pay more if you underestimated the quarterly payments. If there's an overpayment, you can simply apply this to next year's taxes (so no refund and no payment needed).

 
I have a question for the masses. I may have asked here before, but I'm revisiting the question.

My wife (37) is a teacher, has a pension, loves her job and wants to work until 55 (or whenever her plan allows for 85% of her salary).

I have a 401K, Roth IRA, and enough income from rental properties to completely replace my work paycheck. It will actually be about 30% more than what currently make working. I haven't touched any rental income since starting with rentals about 8 years ago. The money has gone toward paying off the loan(s) and/or purchasing additional rentals.

My question is, should I continue to contribute to my IRA? Or even 401K (I know this is free money and will likely take at least the match until I quit working)? Neither of these vehicles will likely play a significant role in my retirement income. Just looking for thoughts/ideas on this.

 
I have a question for the masses. I may have asked here before, but I'm revisiting the question.

My wife (37) is a teacher, has a pension, loves her job and wants to work until 55 (or whenever her plan allows for 85% of her salary).

I have a 401K, Roth IRA, and enough income from rental properties to completely replace my work paycheck. It will actually be about 30% more than what currently make working. I haven't touched any rental income since starting with rentals about 8 years ago. The money has gone toward paying off the loan(s) and/or purchasing additional rentals.

My question is, should I continue to contribute to my IRA? Or even 401K (I know this is free money and will likely take at least the match until I quit working)? Neither of these vehicles will likely play a significant role in my retirement income. Just looking for thoughts/ideas on this.
I feel like the 401k is a no brainer to get at least the match. Depending on the match it is most likely going to destroy any other conservative return you could get.

The Roth IRA is certainly the more tricky question since it involves future use of tax free money when withdrawing. But seeing you said this will not make an affect on your retirement, you could probably skip this if you wanted.

 
random, you have to start with a goal. You mentioned your wife's goal (retire at 55) but what is your goal? If you already have enough income-generating assets to retire today (as you indicate, replace your salary*130% indefinitely) could you retire today? Have you considered health care? Presumably your rentals are inflation indexed (roughly), so you have some protection there.

Start with a goal and work backwards. Maybe you have or want kids, maybe you want to fully fund their schooling, maybe their kids schooling, etc etc

 
random, you have to start with a goal. You mentioned your wife's goal (retire at 55) but what is your goal? If you already have enough income-generating assets to retire today (as you indicate, replace your salary*130% indefinitely) could you retire today? Have you considered health care? Presumably your rentals are inflation indexed (roughly), so you have some protection there.

Start with a goal and work backwards. Maybe you have or want kids, maybe you want to fully fund their schooling, maybe their kids schooling, etc etc
I suppose the goal was to replace the W2 income. I still have a little under a year before the last of the rentals are paid off. We do have 2 kids (3 and 8) that we have been saving to pay for their college. I have somewhat earmarked our IRAs for the college funds if everything works out with the rentals. They each also have 529s we have contributed to off and on.

As for health insurance, I can go on the wifes, as long as I do not have a plan available to me through work.

 
Anyone have a part of their strategy to have stocks with decent dividends (in order to supplement cash flow)? What lead you there?

 
My question is, should I continue to contribute to my IRA? Or even 401K (I know this is free money and will likely take at least the match until I quit working)? Neither of these vehicles will likely play a significant role in my retirement income. Just looking for thoughts/ideas on this.
Oh heck yes. Having a pot of tax deferred income allows you to play tax games and keep lots more of your retirement monies. Since the rentals are all taxable income I'd continue contributing to the 401k at least. Once you retire you can convert the 401k to an IRA and start playing the tax shell game.

Read this and this. Particularly in your case the parts about the conversions.

 
My question is, should I continue to contribute to my IRA? Or even 401K (I know this is free money and will likely take at least the match until I quit working)? Neither of these vehicles will likely play a significant role in my retirement income. Just looking for thoughts/ideas on this.
Oh heck yes. Having a pot of tax deferred income allows you to play tax games and keep lots more of your retirement monies. Since the rentals are all taxable income I'd continue contributing to the 401k at least. Once you retire you can convert the 401k to an IRA and start playing the tax shell game.

Read this and this. Particularly in your case the parts about the conversions.
I've been looking for an article on exactly this. Still have to digest it all, but this will be a huge help :thumbup:

 
My question is, should I continue to contribute to my IRA? Or even 401K (I know this is free money and will likely take at least the match until I quit working)? Neither of these vehicles will likely play a significant role in my retirement income. Just looking for thoughts/ideas on this.
Oh heck yes. Having a pot of tax deferred income allows you to play tax games and keep lots more of your retirement monies. Since the rentals are all taxable income I'd continue contributing to the 401k at least. Once you retire you can convert the 401k to an IRA and start playing the tax shell game.

Read this and this. Particularly in your case the parts about the conversions.
I've been looking for an article on exactly this. Still have to digest it all, but this will be a huge help :thumbup:
There are also some articles on madfientist.com that might be helpful. Nice guides to the tax shell game (all legal - best part!).

 
My mother just informed me she is retiring next year. She asked what I thought she should do with her pension (factory worker at Honda). Her options are 1784/mo (and some other options for a beneficiary) for lifetime or 285K payout. Is there a clear winner in this situation? What else needs to be considered? What are the tax implications for each scenario?

She will be 65 and is in good health. Her mother is 86.

They have no debt and decent savings.

 
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My mother just informed me she is retiring next year. She asked what I thought she should do with her pension (factory worker at Honda). Her options are 1784/mo (and some other options for a beneficiary) for lifetime or 285K payout. Is there a clear winner in this situation? What else needs to be considered? What are the tax implications for each scenario?

She will be 65 and is in good health. Her mother is 86.

They have no debt and decent savings.
That payout will be a brutal tax hit. Could they do it over 2 years...say December 31 and January 1 of the following year? (I doubt you know the answer..just throwing that out there)

 
My mother just informed me she is retiring next year. She asked what I thought she should do with her pension (factory worker at Honda). Her options are 1784/mo (and some other options for a beneficiary) for lifetime or 285K payout. Is there a clear winner in this situation? What else needs to be considered? What are the tax implications for each scenario?

She will be 65 and is in good health. Her mother is 86.

They have no debt and decent savings.
That payout will be a brutal tax hit. Could they do it over 2 years...say December 31 and January 1 of the following year? (I doubt you know the answer..just throwing that out there)
Assuming no, is there any way to minimize the tax hit if they take the payout? Is a IRA rollover available on pensions?

 
My mother just informed me she is retiring next year. She asked what I thought she should do with her pension (factory worker at Honda). Her options are 1784/mo (and some other options for a beneficiary) for lifetime or 285K payout. Is there a clear winner in this situation? What else needs to be considered? What are the tax implications for each scenario?

She will be 65 and is in good health. Her mother is 86.

They have no debt and decent savings.
How "decent" is her savings? 401k? IRA? other? How does the $1784 compare with her monthly costs of living?

 
My mother just informed me she is retiring next year. She asked what I thought she should do with her pension (factory worker at Honda). Her options are 1784/mo (and some other options for a beneficiary) for lifetime or 285K payout. Is there a clear winner in this situation? What else needs to be considered? What are the tax implications for each scenario?

She will be 65 and is in good health. Her mother is 86.

They have no debt and decent savings.
How "decent" is her savings? 401k? IRA? other? How does the $1784 compare with her monthly costs of living?
I will get the answer to this next time I discuss this with them, but for now I can safely assume they have 10+ years of expenses in savings + 401K. They did cash out part of the 401K years ago to payoff the house and buy some adjacent land.

They are fine financially. Between both of their SS checks they can easily cover monthly expenses. They have no debt, and are the type to dive their cars into the ground. They will probably only travel (domestically) once or twice a year.

For now, I'm mostly concerned with helping them decide between payout vs monthly annuity. Obviously the tax situation is the biggest factor here.

 
My mother just informed me she is retiring next year. She asked what I thought she should do with her pension (factory worker at Honda). Her options are 1784/mo (and some other options for a beneficiary) for lifetime or 285K payout. Is there a clear winner in this situation? What else needs to be considered? What are the tax implications for each scenario?

She will be 65 and is in good health. Her mother is 86.

They have no debt and decent savings.
The starting point to figure this out is the risk tolerance of your parents and what other retirement funds they have or don't have. The pension for life is nice because it is backed by the government (PBGC- kind of like the FDIC but for pensions) so it is pretty much as safe as you can get. If this is pretty much their only income other than social security then they may want to consider staying put. By taking the lump sum, they could potentially end up getting better returns but that opens up various levels of risk to potentially achieve that depending on the products that are invested.

I am not an expert on taxes by any stretch but that could or could not be a huge factor. I believe you can roll the pension over into a retirement account to avoid taxes but I am not 100% sure on that.

A big benefit for the lump sum is being able to leave that lump sum to whomever she wishes while pensions usually only available to spouses and usually have to take a lower payout for those options.

Once you decide risk acceptance level then you can figure out what potential products to invest in and likely return on those. There is no real 'right' answer- it is the right answer for your parents situation, wants and needs.

 
My mother just informed me she is retiring next year. She asked what I thought she should do with her pension (factory worker at Honda). Her options are 1784/mo (and some other options for a beneficiary) for lifetime or 285K payout. Is there a clear winner in this situation? What else needs to be considered? What are the tax implications for each scenario?

She will be 65 and is in good health. Her mother is 86.

They have no debt and decent savings.
That payout will be a brutal tax hit. Could they do it over 2 years...say December 31 and January 1 of the following year? (I doubt you know the answer..just throwing that out there)
Or just have the funds sent to an investment house and put into an IRA. Then you pay the taxes on withdrawal, and/or whatever amount of the $285k they want up front.

Basically they should send the entire amount to an IRA to avoid the one-time payment tax hit.

 
My mother just informed me she is retiring next year. She asked what I thought she should do with her pension (factory worker at Honda). Her options are 1784/mo (and some other options for a beneficiary) for lifetime or 285K payout. Is there a clear winner in this situation? What else needs to be considered? What are the tax implications for each scenario?

She will be 65 and is in good health. Her mother is 86.

They have no debt and decent savings.
You can always roll the amount to an IRA. But that's starting to be looked at very closely as the person is giving up the guaranteed payout. What other pension options are there if her spouse is the beneficiary? What happens to the payout if he dies first? What will they get from social security? Does he get a pension?

Over 20 years she will have received over $428,000 with no risk if she takes the annuity.

 
Lump rolled into an IRA is probably the best way to go if you've got 1,000 lifetimes to average, but I think it's closer than many may think.

Life expectancy of a healthy 65 year old female is roughly 20-25 years.

If she starts drawing at 66 and can pull 6% a year, she has to make it 94 before the pension beats the lump sum.

If she starts drawing at 66 and makes 5% a year, the break-even age is 89.

If she starts drawing at 66 and makes 4% a year, the break-even age is 85.

6% is ambitious for someone on a fixed income. If she truly needs this money to live, I'd recommend the pension. There's very small risk that her pension will stop paying out and it's a guaranteed income stream if she makes it to 100, which her life expectancy easily could be if she is in terrific shape (regular exercise, good weight, never smoked, couple of drinks).

Really it comes down to what would happen if she didn't have this money. If she would suffer, she should take the pension. If this is extra money that has a decent chance of not being exhausted, she should take the lump sum and roll into an IRA.

 
Well, not taking into consideration taxes and whatnot, the "break even" point on the pretax dollars is for a lifespan of about 14 more years, so looking at it that way if she took the payout and lived to be 79 she "wins".

However, there are so many factors here. One maybe not mentioned is leaving money to kids if applicable. Good heath can obviously change fast through disease or accident, so to secure a good inheritance the lump sum could be a good way to go.

But all things considered, I would go with the monthly payments. Obvious tax benefit, can still invest, and you know that you will ALWAYS have money coming in no matter what. The monthly annuity seems to be the clear winner for the person of interest, which would be your mother.

 
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Need to keep in mind that with the annuity, you also lose to inflation over time.

That's a pretty decent lump sum if rolled over and invested into a balanced group of securities. I personally would take the lump sum, death ends or significantly reduces an annuity (death benefit).

 
Lump rolled into an IRA is probably the best way to go if you've got 1,000 lifetimes to average, but I think it's closer than many may think.

Life expectancy of a healthy 65 year old female is roughly 20-25 years.

If she starts drawing at 66 and can pull 6% a year, she has to make it 94 before the pension beats the lump sum.

If she starts drawing at 66 and makes 5% a year, the break-even age is 89.

If she starts drawing at 66 and makes 4% a year, the break-even age is 85.

6% is ambitious for someone on a fixed income. If she truly needs this money to live, I'd recommend the pension. There's very small risk that her pension will stop paying out and it's a guaranteed income stream if she makes it to 100, which her life expectancy easily could be if she is in terrific shape (regular exercise, good weight, never smoked, couple of drinks).

Really it comes down to what would happen if she didn't have this money. If she would suffer, she should take the pension. If this is extra money that has a decent chance of not being exhausted, she should take the lump sum and roll into an IRA.
I go with this. The key is whether that monthly amount is critical to her quality of life. The percent return calcs are all straight line which doesn't happen - if the market drops big and your mom has to start pulling out more than 4% - it could lead to draining the nest egg much more quickly.

 
My dad had a similar situation when he divorced my mom. He could pay her X amount forever, but they ended up negotiating a "pay off". I talked my mom into taking the payoff so that she could pay off her condo and also have some extra.

My dad had to live to be like 67 for the break even point. Given the lifespan of males in our family history, it made sense for my mom to take the payoff.

He is now 69 and in seemingly decent health, but my mom technically benfits on the deal as though my dad were to live till about 80, considering there were no taxes on the money, plus she was able to pay off things that she was paying interest on.

In the situation we are discussing here, really, I couldn't fault either side. It's nice to have options, especially when both options are really good options.

 
I've been trying to figure out if there's a formula or more accurate method to figure out how to divide up my retirement contributions as follows:

Work for a Fortune 500 company X, I believe the company has a bright future and is currently attractively priced in the market.

Company match half up to 6%, and if you buy company stock you get it at a 10% discount.

Currently I am doing a 6% contribution to get max match, and also a 3% into company stock.

There has to be some threshold to where the guaranteed initial gain of 10% is not worth being over concentrated on one stock? I'm a believer in diversification, but locking in 10% off the bat on a company I would be investing in even if I didn't work there isn't worth just tossing out without thinking either. Is there some sort of efficient frontier or set of formula's to help guide this decision, or is it just a SWAG at how concentrated you feel like become as an individual?

Some methodology would be great in that as I am able to contribute more, which pile to I put it into as well.

 
My mother just informed me she is retiring next year. She asked what I thought she should do with her pension (factory worker at Honda). Her options are 1784/mo (and some other options for a beneficiary) for lifetime or 285K payout. Is there a clear winner in this situation? What else needs to be considered? What are the tax implications for each scenario?

She will be 65 and is in good health. Her mother is 86.

They have no debt and decent savings.
For a 65 yr old female, an annuity payment of $285K will generate $1550 or so on the free market. The annuity option generates about 15% more cash flow, seems like an obvious choice to me given that she is in good health.

 
I've been trying to figure out if there's a formula or more accurate method to figure out how to divide up my retirement contributions as follows:

Work for a Fortune 500 company X, I believe the company has a bright future and is currently attractively priced in the market.

Company match half up to 6%, and if you buy company stock you get it at a 10% discount.

Currently I am doing a 6% contribution to get max match, and also a 3% into company stock.

There has to be some threshold to where the guaranteed initial gain of 10% is not worth being over concentrated on one stock? I'm a believer in diversification, but locking in 10% off the bat on a company I would be investing in even if I didn't work there isn't worth just tossing out without thinking either. Is there some sort of efficient frontier or set of formula's to help guide this decision, or is it just a SWAG at how concentrated you feel like become as an individual?

Some methodology would be great in that as I am able to contribute more, which pile to I put it into as well.
After you buy the stock at a discount, how long must you hold onto it?

 
Need to keep in mind that with the annuity, you also lose to inflation over time.

That's a pretty decent lump sum if rolled over and invested into a balanced group of securities. I personally would take the lump sum, death ends or significantly reduces an annuity (death benefit).
I think I agree with this. If she were younger, say in her 40s, I'd take the annuity. Why no COLA?

 
I've been trying to figure out if there's a formula or more accurate method to figure out how to divide up my retirement contributions as follows:

Work for a Fortune 500 company X, I believe the company has a bright future and is currently attractively priced in the market.

Company match half up to 6%, and if you buy company stock you get it at a 10% discount.

Currently I am doing a 6% contribution to get max match, and also a 3% into company stock.

There has to be some threshold to where the guaranteed initial gain of 10% is not worth being over concentrated on one stock? I'm a believer in diversification, but locking in 10% off the bat on a company I would be investing in even if I didn't work there isn't worth just tossing out without thinking either. Is there some sort of efficient frontier or set of formula's to help guide this decision, or is it just a SWAG at how concentrated you feel like become as an individual?

Some methodology would be great in that as I am able to contribute more, which pile to I put it into as well.
After you buy the stock at a discount, how long must you hold onto it?
great question. If less than a year, it's a no brainer. If for whatever reason you couldn't sell it while you worked for the company, it's not worth it.

I'd take the guaranteed 10% and sell off a bunch at earliest opportunity.

 
Need to keep in mind that with the annuity, you also lose to inflation over time.

That's a pretty decent lump sum if rolled over and invested into a balanced group of securities. I personally would take the lump sum, death ends or significantly reduces an annuity (death benefit).
I think I agree with this. If she were younger, say in her 40s, I'd take the annuity. Why no COLA?
It would be a virtual certainty that she would not be able to start her pension in her 40s, and if she did the monthly payment would be significantly reduced. And that's not taking into account her desire to manage (or let someone else manage) her money, her risk tolerance, etc.

 

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