Personal Finance Advice and Education!

[matuski]

3 hours ago, Long Ball Larry said:

Not sure if this can really be answered, but  just kind of thinking out loud.

we have an opportunity for an illiquid investment (real estate) that would tie up 60k for 3-5 years.  Offers 9.5% dividend each year with an additional projected 47.5% return at the end.  This would leave us with roughly $15k in cash reserves, which makes me a little nervous as not enough security.

We can build up about $3-5k per month in savings for the foreseeable future and I have another property that I am going to try to sell soon to net some additional cash.  We have Roth IRAs as well, which could theoretically be tapped if any huge emergency.

Does this seem like a safe enough backstop for the return?

no brainer imo.

[wilked]

8 hours ago, Long Ball Larry said:

Not sure if this can really be answered, but  just kind of thinking out loud.

we have an opportunity for an illiquid investment (real estate) that would tie up 60k for 3-5 years.  Offers 9.5% dividend each year with an additional projected 47.5% return at the end.  This would leave us with roughly $15k in cash reserves, which makes me a little nervous as not enough security.

We can build up about $3-5k per month in savings for the foreseeable future and I have another property that I am going to try to sell soon to net some additional cash.  We have Roth IRAs as well, which could theoretically be tapped if any huge emergency.

Does this seem like a safe enough backstop for the return?

Almost makes you wonder why that person isnt keeping such an amazing opportunity for themselves

[ghostguy123]

2 hours ago, wilked said:

Almost makes you wonder why that person isnt keeping such an amazing opportunity for themselves

Right

What exactly is this great opportunity?  Doesnt seem legit.

[Random]

11 hours ago, Long Ball Larry said:

Not sure if this can really be answered, but  just kind of thinking out loud.

we have an opportunity for an illiquid investment (real estate) that would tie up 60k for 3-5 years.  Offers 9.5% dividend each year with an additional projected 47.5% return at the end.  This would leave us with roughly $15k in cash reserves, which makes me a little nervous as not enough security.

We can build up about $3-5k per month in savings for the foreseeable future and I have another property that I am going to try to sell soon to net some additional cash.  We have Roth IRAs as well, which could theoretically be tapped if any huge emergency.

Does this seem like a safe enough backstop for the return?

Would this be completely passive for you?

[Long Ball Larry]

45 minutes ago, Random said:

Would this be completely passive for you?

Yes

[Long Ball Larry]

3 hours ago, wilked said:

Almost makes you wonder why that person isnt keeping such an amazing opportunity for themselves

It’s a pooled real estate investment for accredited investors and one of the principals has been a friend of me and my wife for about 20 years.  He has done several real estate deals.

i have no illusions about the possibility that the investment won’t pan out with the projected returns, though looking through the prospectus I think that it is a reasonable median outcome.   My only concern is that i have never really put this much cash on ice at one time.

[SFBayDuck]

On 2/13/2020 at 5:47 AM, CR69 said:

It is crazy, but I see it every day. Just yesterday I got some pre-approved to buy a house. They make $200k a year and are having to get a gift for their $25k down payment...

That’s pretty much me. I drive a 10 year old car, we live in a small 4-bedroom rental house that is one of the best deals in town, and I haven’t been on a tropical vacation that wasn’t paid for by work in years. The only “extravagance” in terms of spending is private high school for my daughter. But the cost of living is just so damn high here that it’s hard to save, outside of maxing my retirement accounts. And it’s not just housing, which is ridiculous, it’s everything - $400/month for gas/electric (don’t even have a/c), gas is $.50-$1.00 more a gallon, restaurants or a cocktail or two (which we don’t do often) are double what they are elsewhere, and a combo of high state taxes and sales taxes. Throw in child support (even though I have 50/50 custody and the ex is long remarried), and many months I do coast into the next paycheck on fumes. 

 

 

[-OZ-]

15 hours ago, Long Ball Larry said:

Not sure if this can really be answered, but  just kind of thinking out loud.

we have an opportunity for an illiquid investment (real estate) that would tie up 60k for 3-5 years.  Offers 9.5% dividend each year with an additional projected 47.5% return at the end.  This would leave us with roughly $15k in cash reserves, which makes me a little nervous as not enough security.

We can build up about $3-5k per month in savings for the foreseeable future and I have another property that I am going to try to sell soon to net some additional cash.  We have Roth IRAs as well, which could theoretically be tapped if any huge emergency.

Does this seem like a safe enough backstop for the return?

If you fully trust the people and make the right contract, I'd be on board. 

[joey]

Another finance thread? Ugh. In, I guess  

[NutterButter]

Is this how all those professional athletes go broke?   It always seems they lose their shirts in real estate.   

[Sand]

7 hours ago, SFBayDuck said:

That’s pretty much me. I drive a 10 year old car, we live in a small 4-bedroom rental house that is one of the best deals in town, and I haven’t been on a tropical vacation that wasn’t paid for by work in years. The only “extravagance” in terms of spending is private high school for my daughter. But the cost of living is just so damn high here that it’s hard to save, outside of maxing my retirement accounts. And it’s not just housing, which is ridiculous, it’s everything - $400/month for gas/electric (don’t even have a/c), gas is $.50-$1.00 more a gallon, restaurants or a cocktail or two (which we don’t do often) are double what they are elsewhere, and a combo of high state taxes and sales taxes. Throw in child support (even though I have 50/50 custody and the ex is long remarried), and many months I do coast into the next paycheck on fumes. 

In all fairness you live in the single most expensive place in the country.  

[Sand]

10 hours ago, ghostguy123 said:

Right

What exactly is this great opportunity?  Doesnt seem legit.

[Random]

21 hours ago, Long Ball Larry said:

Not sure if this can really be answered, but  just kind of thinking out loud.

we have an opportunity for an illiquid investment (real estate) that would tie up 60k for 3-5 years.  Offers 9.5% dividend each year with an additional projected 47.5% return at the end.  This would leave us with roughly $15k in cash reserves, which makes me a little nervous as not enough security.

We can build up about $3-5k per month in savings for the foreseeable future and I have another property that I am going to try to sell soon to net some additional cash.  We have Roth IRAs as well, which could theoretically be tapped if any huge emergency.

Does this seem like a safe enough backstop for the return?

So you're getting a $90K ARV rental property that needs 10K in repairs for 50K.  Rents are 800-900 less expenses netting you 5700/yr.  Doesn't seem unreasonable.

Edited February 17, 2020 by Random

[Long Ball Larry]

14 minutes ago, Random said:

So you're getting a $90K ARV rental property that needs 10K in repairs for 50K.  Rents are 800-900 less expenses netting you 5700/yr.  Doesn't seem unreasonable.

on a much much larger scale, but yes, more or less correct.

[Random]

41 minutes ago, Long Ball Larry said:

on a much much larger scale, but yes, more or less correct.

Right but your share is $60K so I went off that.  I would say the 47% return in 3-5 years is the most uncertain, esp if you're talking about commercial RE.

Edited February 17, 2020 by Random

[ghostguy123]

41 minutes ago, Long Ball Larry said:

on a much much larger scale, but yes, more or less correct.

Didnt you say this was passive?  

[Gawain]

Wondering if anyone wants to give advice on a couple of jobs:

Job A: 87K + 5% bonus. Roughly 50 hours a week and 50 min commute each way each day. Very stable. Growth path to my bosses job (110-125) in the next 3-5 years.

Job B: 110K + 6% bonus. Roughly 45 hours a week working from home. Traveling away from home 12 weeks out of the year. 2 year contract, but very unstable afterwards. No growth path.

Left Job B 4 months ago because I was moving. Liked the job/boss. Received a call from him on Friday saying my replacement wasn't working out and they want me back.
Have three kids; 3, 2, 7 months. Wife is SAHM. Decent amount of support around us.

Realize not the right thread, but value the opinions of a lot of posters in here.

[SFBayDuck]

1 hour ago, Sand said:

In all fairness you live in the single most expensive place in the country.  

True, and there’s a reason for that, it’s awesome here.  Today after my morning trail run we went to the beach, then ate lunch outside.  But it obviously comes with some pretty significant financial trade-offs for those of us non-hedge fund, VC, or CEO types. 

[NutterButter]

1 hour ago, Gawain said:

Wondering if anyone wants to give advice on a couple of jobs:

Job A: 87K + 5% bonus. Roughly 50 hours a week and 50 min commute each way each day. Very stable. Growth path to my bosses job (110-125) in the next 3-5 years.

Job B: 110K + 6% bonus. Roughly 45 hours a week working from home. Traveling away from home 12 weeks out of the year. 2 year contract, but very unstable afterwards. No growth path.

Left Job B 4 months ago because I was moving. Liked the job/boss. Received a call from him on Friday saying my replacement wasn't working out and they want me back.
Have three kids; 3, 2, 7 months. Wife is SAHM. Decent amount of support around us.

Realize not the right thread, but value the opinions of a lot of posters in here.

With Job B, how much of a plus or minus is the traveling.     I guess same goes for the SAH with your wife and maybe kids being there all the time.  Meaning, I know if my wife was SAHM and I had two young kids there as well, I'll rather go into the office.  In addition, some people don't value SAH as much.  Me personally, I like going into the office at least a few days a week and essentially socializing.  Is the salary difference really gonna come in handy or is it more disposable income?   How comfortable do you feel about getting another job at least in a manageable salary range after the 2 years?

Edited February 17, 2020 by NutterButter

[ghostguy123]

1 hour ago, Gawain said:

Wondering if anyone wants to give advice on a couple of jobs:

Job A: 87K + 5% bonus. Roughly 50 hours a week and 50 min commute each way each day. Very stable. Growth path to my bosses job (110-125) in the next 3-5 years.

Job B: 110K + 6% bonus. Roughly 45 hours a week working from home. Traveling away from home 12 weeks out of the year. 2 year contract, but very unstable afterwards. No growth path.

Left Job B 4 months ago because I was moving. Liked the job/boss. Received a call from him on Friday saying my replacement wasn't working out and they want me back.
Have three kids; 3, 2, 7 months. Wife is SAHM. Decent amount of support around us.

Realize not the right thread, but value the opinions of a lot of posters in here.

Negotiate 125k and 10% bonus with 4 year contract

Also depends if you even want your bosses job with your current place

Edited February 17, 2020 by ghostguy123

[Gawain]

8 minutes ago, NutterButter said:

With Job B, how much of a plus or minus is the traveling.     I guess same goes for the SAH with your wife and maybe kids being there all the time.  Meaning, I know if my wife was SAHM and I had two young kids there as well, I'll rather go into the office.  In addition, some people don't value SAH as much.  Me personally, I like going into the office at least a few days a week and essentially socializing.  Is the salary difference really gonna come in handy or is it more disposable income?   How comfortable do you feel about getting another job at least in a manageable salary range after the 2 years?

Traveling is a pain, but probably at least outweighed by the fact that I'd be WFH three weeks out of the month. Currently I'm out the door at 6 AM and home between 5-7 PM. With job B, I'd be around to help the kids get up and get breakfast and then help with lunch. My current position doesn't have much in the way of socialization, as it's either my boss or people I manage on site.

I've been thinking that the salary bump would go towards funding an MBA over the next two years. If so, I'd anticipate being at least as employable in 24 months.

1 minute ago, ghostguy123 said:

Negotiate 125k and 10% bonus with 4 year contract

As I laid it out, this is the best I could do (reason I'm in operations and not sourcing)

 

Edited February 17, 2020 by Gawain

[ghostguy123]

3 minutes ago, Gawain said:

 

As I laid it out, this is the best I could do (reason I'm in operations and not sourcing)

 

Do you want your bosses job?

[Gawain]

4 minutes ago, ghostguy123 said:

Do you want your bosses job?

Yeah, though there's a reason my boss and his boss are both on their second marriages (long hours). I'd prefer to avoid that.

[NutterButter]

24 minutes ago, Gawain said:

Yeah, though there's a reason my boss and his boss are both on their second marriages (long hours). I'd prefer to avoid that.

So the hours are even longer with your boss's job?   That a pretty long day with A as it is. 

[Gawain]

4 minutes ago, NutterButter said:

So the hours are even longer with your boss's job?   That a pretty long day with A as it is. 

Probably about the same, but it's 24/5 responsibility so going into the night is uncommon, but not rare.
 

[joey]

2 hours ago, SFBayDuck said:

True, and there’s a reason for that, it’s awesome here.  Today after my morning trail run we went to the beach, then ate lunch outside.  But it obviously comes with some pretty significant financial trade-offs for those of us non-hedge fund, VC, or CEO types. 

I’m with you. 
non-CEO/non-hedge fund guy here. 
 

luckily we’ve owned since 2001 (even then, parents said to Mrs and I, “you’re paying WHAT for a 4 BR house?!?!). 
 

now that we’re single income, it’s hard to save more than maxing out 401k and IRA, $250/mo for 2 kids 529’s. Used to save a few $k more each year besides that but the recent tax changes now chews that up. 
 

all that said, wouldn’t want to live anywhere ride. Thinking of downsizing in 8 years when youngest graduates high school (moving 30 miles further north of SF). Love it around here. 

Edited February 17, 2020 by joey

[culdeus]

On 2/11/2020 at 4:30 AM, pollardsvision said:

For most. But there are some that really only see it as an investment vehicle. 

Withdrawals for reimbursements for medical expenses can be drawn during a later tax year, and there's currently no limit to what "later" means. So, you can pay current medical expenses out of pocket, keep good receipts and records, then say, 20 years from now, go ahead and take the withdrawals to reimburse. So, you pay for the medical expenses, but still get the tax-free growth from having it invested long-term.

 

There are good arguments for making your HSA your absolute wheels off high risk account.  If it ####s the bed fall back to something else. 

[culdeus]

On 2/11/2020 at 4:30 AM, pollardsvision said:

For most. But there are some that really only see it as an investment vehicle. 

Withdrawals for reimbursements for medical expenses can be drawn during a later tax year, and there's currently no limit to what "later" means. So, you can pay current medical expenses out of pocket, keep good receipts and records, then say, 20 years from now, go ahead and take the withdrawals to reimburse. So, you pay for the medical expenses, but still get the tax-free growth from having it invested long-term.

 

There are good arguments for making your HSA your absolute wheels off high risk account.  If it ####s the bed fall back to something else. 

[ConstruxBoy]

11 hours ago, SFBayDuck said:

True, and there’s a reason for that, it’s awesome here.  Today after my morning trail run we went to the beach, then ate lunch outside.  But it obviously comes with some pretty significant financial trade-offs for those of us non-hedge fund, VC, or CEO types. 

I just assumed you were the CEO of a VC hedge fund...

[CR69]

22 hours ago, SFBayDuck said:

That’s pretty much me. I drive a 10 year old car, we live in a small 4-bedroom rental house that is one of the best deals in town, and I haven’t been on a tropical vacation that wasn’t paid for by work in years. The only “extravagance” in terms of spending is private high school for my daughter. But the cost of living is just so damn high here that it’s hard to save, outside of maxing my retirement accounts. And it’s not just housing, which is ridiculous, it’s everything - $400/month for gas/electric (don’t even have a/c), gas is $.50-$1.00 more a gallon, restaurants or a cocktail or two (which we don’t do often) are double what they are elsewhere, and a combo of high state taxes and sales taxes. Throw in child support (even though I have 50/50 custody and the ex is long remarried), and many months I do coast into the next paycheck on fumes. 

 

 

I should have added that I live in an area where the median income is about $67k and you can find a decent house to live in for $250-300k. 

I understand people in expensive cities like NYC, SF, etc living paycheck to paycheck when they’re making $200k

[culdeus]

Well I'm at the time of the year where I reshuffle everything.  Bonuses all came in and life is good.   I still struggle this time of year figuring out if I should allocate retirement funds differently than main savings.    

I'm mid 40s and after last year and the years prior I'm way ahead of schedule retirement wise.  Maybe by 8 or more years.   Does that change things?   I can now realistically see myself calling it at 55 or having my wife quit at 50 and going onto 60.  

I never see this topic discussed.  

[Random]

21 minutes ago, culdeus said:

Well I'm at the time of the year where I reshuffle everything.  Bonuses all came in and life is good.   I still struggle this time of year figuring out if I should allocate retirement funds differently than main savings.    

I'm mid 40s and after last year and the years prior I'm way ahead of schedule retirement wise.  Maybe by 8 or more years.   Does that change things?   I can now realistically see myself calling it at 55 or having my wife quit at 50 and going onto 60.  

I never see this topic discussed.  

Lots of things factor into this.  

Do you like your job (what is it you do)?

Does your wife like her job?

Stress level of jobs?

Other income sources?

House paid off?

Do you have kids (and are college plans take care of)?

 

[Sand]

10 hours ago, culdeus said:

There are good arguments for making your HSA your absolute wheels off high risk account.  If it ####s the bed fall back to something else. 

The current administration (keeping this politics neutral) is knocking around an idea for a new tax advantaged account.  According to this - "Money put into the account would be done so on an after-tax basis, and taxed when withdrawn as well; but any accumulation of profits during the investment timeframe, known as capital gains, would not be taxed."

Yeah, they might as well name it the GBGH account.  I'd put a bit in there and take a number of moonshots with this vehicle, join the Furley investment club, dream of TVIX every night, etc.

[Random]

On 2/15/2020 at 10:14 PM, Long Ball Larry said:

Not sure if this can really be answered, but  just kind of thinking out loud.

we have an opportunity for an illiquid investment (real estate) that would tie up 60k for 3-5 years.  Offers 9.5% dividend each year with an additional projected 47.5% return at the end.  This would leave us with roughly $15k in cash reserves, which makes me a little nervous as not enough security.

We can build up about $3-5k per month in savings for the foreseeable future and I have another property that I am going to try to sell soon to net some additional cash.  We have Roth IRAs as well, which could theoretically be tapped if any huge emergency.

Does this seem like a safe enough backstop for the return?

Pretty sure I'd pass on this.  Return is no better than getting 13% compounded for 5 years on your 60K.  Is there more or less risk here than a typical sp500 index fund?  Might be ok if you're looking for diversification, but I wouldn't consider this a home run.

[ConstruxBoy]

1 hour ago, Random said:

Lots of things factor into this.  

Do you like your job (what is it you do)?

Does your wife like her job?

Stress level of jobs?

Other income sources?

House paid off?

Do you have kids (and are college plans take care of)?

 

Also don’t forget healthcare until Medicare

[culdeus]

2 hours ago, Random said:

Lots of things factor into this.  

Do you like your job (what is it you do)?    Yes, I'd keep at this for decades if I could. 

Does your wife like her job?  Yes but it is stressful and she's in a cycle where she's constantly asked to do more with little in return. 

Stress level of jobs?  Mine is seasonally stressful, but manageable.  

Other income sources?  I do anticipate some inheritance, mostly in the form of mineral royalties that will provide cash flow.  I'm thinking of that as a bonus now as the stability of that cash flow for 40 years is in question given the political environment.  If lets say that came due tomorrow with the prices as they are it would roughly replace my wife's salary.  

House paid off?  No, but that's a priority to speed that up. At interest rates this low I'm just hesitant to do it and take that money out of the stock market.  

Do you have kids (and are college plans take care of)?  Kids college is more than done now, with the stock market run-up.  I won't give them another dime, and if they blow through all this it's on them.  

There was also a followup question on medical till medicare, if I can manage to stay on at my job thru this year I'll be eligible to buy into the work health plan at the employee rate for life.  That is a massive benefit. 

[Long Ball Larry]

2 hours ago, Random said:

Pretty sure I'd pass on this.  Return is no better than getting 13% compounded for 5 years on your 60K.  Is there more or less risk here than a typical sp500 index fund?  Might be ok if you're looking for diversification, but I wouldn't consider this a home run.

thank you.  this is exactly the kind of bottom line that i was trying to meander toward.  fundamentally, how to quantify the opportunity cost and the illiquidity premium.  very helpful way to think about it for me.

[Binky The Doormat]

3 hours ago, Random said:

Pretty sure I'd pass on this.  Return is no better than getting 13% compounded for 5 years on your 60K.  Is there more or less risk here than a typical sp500 index fund?  Might be ok if you're looking for diversification, but I wouldn't consider this a home run.

give me a locked in 13% and I'll take it all. @Long Ball Larry please PM me.  

please.  

[Random]

33 minutes ago, Binky The Doormat said:

give me a locked in 13% and I'll take it all. @Long Ball Larry please PM me.  

please.  

I highly doubt its locked in.

[Long Ball Larry]

6 hours ago, Binky The Doormat said:

give me a locked in 13% and I'll take it all. @Long Ball Larry please PM me.  

please.  

i mean, i think that it is more likely than not, but by no means locked in.

[ghostguy123]

5 hours ago, Random said:

I highly doubt its locked in.

So where is a better place to put that money?

[Sand]

8 minutes ago, ghostguy123 said:

So where is a better place to put that money?

TVIX.  The answer is always 42 TVIX.

[DocHolliday]

On 2/16/2020 at 8:36 PM, Gawain said:

Wondering if anyone wants to give advice on a couple of jobs:

Job A: 87K + 5% bonus. Roughly 50 hours a week and 50 min commute each way each day. Very stable. Growth path to my bosses job (110-125) in the next 3-5 years.

Job B: 110K + 6% bonus. Roughly 45 hours a week working from home. Traveling away from home 12 weeks out of the year. 2 year contract, but very unstable afterwards. No growth path.

Left Job B 4 months ago because I was moving. Liked the job/boss. Received a call from him on Friday saying my replacement wasn't working out and they want me back.
Have three kids; 3, 2, 7 months. Wife is SAHM. Decent amount of support around us.

Realize not the right thread, but value the opinions of a lot of posters in here.

Go with job B.   Enjoy the time spent with the kids and get that MBA.   Sounds like you don’t really like job A and don’t really want the bosses job.    

[Random]

10 hours ago, ghostguy123 said:

So where is a better place to put that money?

Hard to say without knowing his entire financial landscape and the risk associated with the investment.  Maybe a REIT?

Edited February 18, 2020 by Random

[Nugget]

On 2/11/2020 at 4:30 AM, pollardsvision said:

For most. But there are some that really only see it as an investment vehicle. 

Withdrawals for reimbursements for medical expenses can be drawn during a later tax year, and there's currently no limit to what "later" means. So, you can pay current medical expenses out of pocket, keep good receipts and records, then say, 20 years from now, go ahead and take the withdrawals to reimburse. So, you pay for the medical expenses, but still get the tax-free growth from having it invested long-term.

 

I think the HSA is becoming by emergency cash fund.  I am paying for medical costs out of normal income, but saving the receipts in case I need to cash out for an unexpected expense.  I put $600 month in and 80% goes into index funds.  

Think my new saving strategy is:

• 401K contribution to get maximum employer match
• Max HSA contribution (20% fairly liquid until overall balance is $25K)
• Max Roth IRA
• Combo of 401K contribution and taxable investment funds - not sure on the balance between these two

[SFBayDuck]

2 hours ago, Nugget said:

I think the HSA is becoming by emergency cash fund.  I am paying for medical costs out of normal income, but saving the receipts in case I need to cash out for an unexpected expense.  I put $600 month in and 80% goes into index funds.  

 

Am I right in that the only need for documentation for an HSA reimbursement is if you are ever audited?  I'm used to the FSA where I had to submit the receipts to get reimbursement, but as I'm doing my taxes for the first time with an HSA TurboTax just asked me the question of whether the funds were for medical expenses.  They were, but I just want to be clear on the requirements.

[Nugget]

7 minutes ago, SFBayDuck said:

Am I right in that the only need for documentation for an HSA reimbursement is if you are ever audited?  I'm used to the FSA where I had to submit the receipts to get reimbursement, but as I'm doing my taxes for the first time with an HSA TurboTax just asked me the question of whether the funds were for medical expenses.  They were, but I just want to be clear on the requirements.

I've had an HSA since 2009, but I just used the debit card provided whenever I had a medical expense.  I am hopeful that between EOBs and receipts I should be good for future reimbursements or audits.  When I've filled my taxes in the past, I just submit form 8889 and move the HSA contribution to Schedule 1.  They've never asked me for any additional documentation.

[-OZ-]

18 minutes ago, Nugget said:

I've had an HSA since 2009, but I just used the debit card provided whenever I had a medical expense.  I am hopeful that between EOBs and receipts I should be good for future reimbursements or audits.  When I've filled my taxes in the past, I just submit form 8889 and move the HSA contribution to Schedule 1.  They've never asked me for any additional documentation.

I don't have an HSA, not eligible. But I was listening to a podcast the other day, the podcaster commented that a smart move is to just keep your medical receipts, pay out of pocket, then if you really need the funds you can just use the receipt from years ago to justify the withdrawal.  I had assumed the expense would have to be in the same year as the withdrawal, but that seems to be incorrect.

[SFBayDuck]

19 minutes ago, -OZ- said:

I don't have an HSA, not eligible. But I was listening to a podcast the other day, the podcaster commented that a smart move is to just keep your medical receipts, pay out of pocket, then if you really need the funds you can just use the receipt from years ago to justify the withdrawal.  I had assumed the expense would have to be in the same year as the withdrawal, but that seems to be incorrect.

Yeah I'd heard that part, that's what makes it such a great thing - tax free going in and coming out, and you can use it years down the line.  To me that'd be the real win if you can swing it - build it up over years to a sizable amount and have it available to either pay for medical expenses during retirement or to supplement retirement income by reimbursing yourself for past expenses.

I just wasn't sure on the logistics for reimbursement other than "keep all your receipts".

[Buckna]

Not sure which thread I posted it in, but make sure to scan your receipts, the ink sometimes fades very quickly. Many HSA providers will let you upload and save the receipt images without having to claim a reimbursement... or you can just stick them in the cloud. Honestly, it would be a good idea to do this for regular taxes as well, I've seen receipts fade to unreadable within the span of weeks.