Well I was in GD and looking around, didn't think my employer had any plans that had an HSA account.  I posted in a thread but since I would like to be more specific to make my determination on how well it will work for me here I am....

This is what I posted in the GD thread:

Okay I have been looking and didn't think I had the option of getting a health insurance plan with an HSA.  I actually have just a couple of options.  Now before I get hammered on the downsides most of medical is covered from my misfortunes in working for uncle sam in the sandbox.  I do have exceptions but overall medical deductibles are usually not an issue.  Though I will be more careful if I go the HSA route knowing I could eat a really big bill if something drastic happens and I haven't knocked down my deductible yet.

I currently max out the 19.5k 401k limit and the 6k limit on a ROTH.  I send a few bucks here a month to a Fidelity account as well.  I would like to know the important numbers and how this actually works before I make a different selection on health care.  I really want to know the max I can put into one and what each of the deductibles mean.  I saw others say they put 10k into their HSA but I am single and not sure how much it will really help me.  Once its in an HSA account how to you invest it or would it just sit there tax free until I am able to pull it out?

The math I see so far for each HSA plan (there are other plans listed in this category but all of them are HRA plans but that looks like a really bad idea):

Annual Deductible: $1500 in network or $3000 for out of network -(other option)- $2000 for both in and out of network
Medical account contribution: $900 (or) $1200
Net deductible: $600 or $2100 out of network (or) $800
Max out of pocket annual: $5000 or $7000 (or) $6000 or $7500

Also I currently put money into my FSA account annual for stuff like glasses, I assume I can still do this as well having an HSA plan?  I don't think it works that way but would be nice.
[end quote]

I totally get the tax advantage but still not sure how the HSA is a "triple win."  Say I saved 25-36% tax on a few dollars, can I invest it right away the next year or does it have to sit until I am 65 to play with it?  If it has to sit there then inflation will ruin it plus any percent I might gain in an investment account.  I see others say they are putting in 10k but I am single so my limits are probably much lower than a family unit.  I currently spend a baseline of $450 a year out of my FSA account for glasses and other medical things.  If I get hit with a big bill it will come out of the $500 I am able to carry over from my FSA account.

In short:

$7150 (annual max contribution for family) goes in pre-tax, grows tax free (assuming you move it into something other than cash), and comes out tax free if used for eligible medical, dental, vision expenses. Can also be used to pay for things like long term care insurance premiums, COBRA premiums, or Medicare advantage premiums. Once you reach age 65, funds can be used for non-eligible expenses but will be taxed as regular income.

You cannot contribute to a standard FSA and HSA simultaneously. However, if your employer offers a Limited purposes FSA (LMSA - covers only dental, vision, and preventative care) you can contribute to LMSA and HSA simultaneously. I’m doing this right now, paying for a kids braces with LMSA while hoarding tax-free income in the HSA.

ETA: I have the highest deductible option my employer offers because it’s cheap and we never use our medical insurance. The only regular expense I have is chiropractic visits. Even though my insurance policy will never pay a dime for those visits they negotiated a “preferred provider” rate with my chiropractor so now I’m only paying $30 per visit instead of $50.

HSA is great.  I use mine to pay all my medical expenses each year with pretax dollars.  I put in $2600 and my company gives me $1000.  I'm pretty young but even basic shit is expensive as hell.  I had some skin biopsies done a few weeks ago.  It cost $800.  I have $1000 in my HSA so I'm good.  I only gained access to HSA two years ago.  It's helped a lot with shit like that the last two years.

Lower your taxable income and pay medical bills with pretax dollars.  It's awesome.

My FSA account can do the same its just that I can only carry over $500 a year or I lose what ever is over that amount.  I want to say I can put up to 3k in it a year but unless I buy 87 million condoms I wouldn't use it all.  With the HSA you can use it for medical expenses but you can keep anything you do not use.  I guess I have to look to see what the each HSA offers as far as investing but so far can't find much but a "cash account."  That doesn't let it grow like I would want....  I could use it to pay part B of my Medicare when I hit 65 though.  Depending on how much I am withdrawing from other accounts will determine how much I have to pay each month.  

It almost takes a rocket scientist to calculate all the variables I will have.  Between a small pension, reserve military retirement, and the SS funds after 2030 I have no clue how much I will actually need to withdraw to live.  I hope maybe I don't need any of it but at age like 72 or something I get fucked if I don't start taking it sooner so the MRD doesn't send me to a different tax bracket.

Your HSA provider is like your 401k provider, they provide a suite of mutual funds you can invest in.

HSA accounts have other advantages over 401k accounts for retirement and financial planning:
- HSA's have no RMD's,
- HSA contributions are exempt from FICA taxes, where IRA and 401K contributions are not,
- As long as the withdrawal covers an approved expense (and you listed them above) you can take money out of your HSA at any age, you don't have to wait until you are 59.5 years old,
- You don't have to immediately pay for your out of pocket medical expenses with HSA funds if you don't want to.  If you wish you can pay current medical bills using post-tax dollars, set the bill aside, and 3... 5... 10... etc. years you can reimburse yourself for that medical bill, and all the while that money will have been in your HSA earing tax-free investment interest for years.  That reimbursement does not count as income since you used it to offset a medical expense, even if it takes years before you pay yourself back.

I guess I need to find what mutual funds each plan has, not sure if that is available .....if it is I haven't found it.  I will have to ask my HR person this week for more information.  Just to clarify if you put say $3000 grand in an HSA this year and nothing else period.  You had it in an fund that turned your 3k into 15k when you hit age 60.  You can pull out that 3k of expenses you acquired during this time but if you don't have any other bills to show for the 12k left you will pay the taxes on it?

My HSA account at TDAmeritrade is self administered. I can invest or trade any stocks, ETFs or mutual funds. There was an option for them to run it but I chose to run my own. I went through HSA Bank and they set up the account at TD. I even have debit card from them. 1k in cash had to remain in the HSA bank account.

Only if you withdraw the additional $12k without using it to offset other medical expenses.  I would just leave it in the HSA account to continue growing tax-free; most of us need more and more medical care as we age.  If I die before it's all used up then it goes to the listed beneficiary on the account just like a 401k, IRA, etc.

I will qualify for Tricare at age 60 until Medicare takes over at 65.  So part A of my Medicare will be covered for free.  Part B I believe depends on your taxable income from the previous year.  The current minimum premium is $148.50 a month.  If you make over 88k then it goes to $207.50 a month, over 111k then its $297.50 a month, etc.  Between my small pension, mil retirement, and trying to estimate my SS I will be at roughly 60k of taxable income.  The last few years my 401k has grown over 30k just in gains each year.  I know that some years I will take 50k plus in losses but I still have 15 years of contributions to help my account grow even more.  I am not sure what the tax brackets will be but I would like to stay below the 24% rate but for sure the 32% rate.  I see myself having to start taking my 401k money when I fully retire so if/when I hit 72 I do not get bent over by uncle sam.  I will then take and buy more mutual funds or other investments.  

It says on the website that my Medicare premium will be taken directly out of my SS or for me my mil retirement check.  I know this might be "not the norm" for most of my medical care will be covered by the VA at this point (my service connected conditions have a 99% track record of getting worse).  Besides Medicare coverage I might not have very many payments for medical expenses and not sure if I can get these paid for by my HSA instead of automatic withdraw from my SS or mil retirement.

The fact I can treat this like a 401k and it reduces my taxable income is good.  Then the fact I wouldn't have to take an MRD like my 401k is great.  

As a note, single and don't planned to be married again, no kids currently and for sure not planned.

https://www.whitecoatinvestor.com/7-reasons-an-hsa-should-be-your-favorite-investing-account/

Can 1 account cover yourself and spouse or must each have their own account?

Based on looking up the FSA rules it appears you can have a single plan or a family plan.  If you choose the family plan you can put 2x the amount in an HSA.  Think the limit is 3.5k for single and 7k for a family plan.  What I don't know is if possible to have say yourself on a family plan with kids and your wife have a separate single plan for her (or vise versa).  If someone did this they would be paying for a healthcare plan that may cost several thousand each year just to put money in an HSA possibly.  Not sure an other legal qualifications either.

I am not the best person to answer but maybe this helped or will bring a correct answer to the table.

HSA is the best deal ever.  Treat it like a separate bonus 401k, because that's what it really is - but better.  When you retire, you can draw from it just like a 401k; which of course you pay taxes on as income just like 401k.  BUT, if your withdraw is for medical expenses, that is tax free.

And for medical expense now while you are still contributing; pulling out of HSA should be viewed the same as pulling out of your 401k.   If you need to, to pay the bills, great - that's what it's there for.  But if you have enough cash to just pay for the medical bills out of pocket, do that.  Your cash isn't working for you, and is frankly being devalued something fierce right now.  Your HSA funds though are on the market (which you need to make sure to do), just like 401k, so are accuring and compounding, just like a 401k.  

Even better, HSA can be contributed still half way into the next year, and often has some level of employer matching  as well.

As to limits, it's confusing, but basically between you and spouse you get ~$7.5k (or whatever).  You can do combined family, or individual for half that, or I think (maybe) even one can have family and the other individual, but no matter what, you can't got over the $7.5k combined.

As to exposure to the high deductible; that risk is way overstated.  Your premiums are so much lower that just saving that difference will cover much of the way to the deductible cap, after which insurance starts kicking in just like regular full-coverage insurance.  Under no circumstances should you start a High Deductible coverage plan without also contributing to an HSA.

Frankly, I think you should max out your HSA faster than maxing out your 401k, because it IS a 401k; that you can also use for tax-free medical bill payment.

Wait... what??!  You can do that??!

If you can account for a medical expense while you had the account you can pull the money out at any time tax free.  The fact that the 2k in medical expenses you didn't withdraw is now worth 5k means you can take out the 2k tax free but the 3k you made money on you have to pay taxes on unless it falls under a different medical expense.  If it is not a medical expense you do have to wait until you turn 65 to get the funds and pay the tax though.  I hear to make sure you keep all your receipts though, not sure if anyone has been audited for this.

Yea I get that - that part is text-book.  The part I'm excited by, is the statement that I can do medical expenses now.  Pay for them out of pocket (cash out of normal checking account) right now.  Then keep the receipt.  Then, when I retire in a 30 years, I can draw out of my HSA 30 years from now, that 30 year old expense, and draw it tax free then?  I just assumed it had to be same year, or close to it.  If not, that's a big deal; is why I ask.

Yes, which is why an HSA is such a powerful retirement planning tool if you start it when you are young and healthy: you can reimburse yourself any time, even after you retire, and there is no tax due on the reimbursement.  Just keep your receipts.

Yep, then if you want to you can call it an emergency fund.

Tax break when money goes in, grows tax free, pay from a regular account - save your receipts and let the money continue to grow in the HSA, then take the money out at a time of your choosing tax free.

After a certain age can take the money out for anything but you have to pay taxes.

It’s probably the best type of account for tax savings since money for health expenses goes in tax free, grows tax free, and comes out tax free.

The above poster pretty much nails it.  For me, HSA makes a lot of sense because the lower monthly pay check contributions to the actual healthcare cost are nice, and I don't need a lot of medical - like a once a year physical that is covered in full, and some maintenance meds that are cheap.  So I pretty much bank the HSA contribution from my employer ($900 a year for single coverage if I do my wellness part), plus another $2500 or so tax free on my part to get close to the annual single coverage limit.  I've been in a plan like this since 2011, now have an HSA balance of $24k, as I did have a couple of years where I hit the deductible due to unplanned incidents.  I keep about $22k in play in the market, with just enough cash on hand to cover my deductible and out of pocket max.  If my experience and trend model play out, I'll have about $250k in my HSA when I retire in 20 years, and can either use that for medicare premiums, or just as retirement income.  A great thing about the HSA is portability, started mine with one employer, ported it to the next since the balance is always your money.

The above poster pretty much nails it.  For me, HSA makes a lot of sense because the lower monthly pay check contributions to the actual healthcare cost are nice, and I don't need a lot of medical - like a once a year physical that is covered in full, and some maintenance meds that are cheap.  So I pretty much bank the HSA contribution from my employer ($900 a year for single coverage if I do my wellness part), plus another $2500 or so tax free on my part to get close to the annual single coverage limit.  I've been in a plan like this since 2011, now have an HSA balance of $24k, as I did have a couple of years where I hit the deductible due to unplanned incidents.  I keep about $22k in play in the market, with just enough cash on hand to cover my deductible and out of pocket max.  If my experience and trend model play out, I'll have about $250k in my HSA when I retire in 20 years, and can either use that for medicare premiums, or just as retirement income.  A great thing about the HSA is portability, started mine with one employer, ported it to the next since the balance is always your money.

I would like to know how this is done.  I will have a military retirement check when I get to that age.  When I hit 65 Medicare part A is taken care of but part B will be automatically taken out of my check if I read everything correctly.  What I don't know is if the Medicare is taken out tax free when that happens.  If it is not can you get an HSA to cover it I can keep all of my retirement check and use my HSA account for Medicare?  I also understand they base your Medicare part B off last years taxable income.  Currently Medicare part B charges if you are single (roughly rounded to the nearest $5 bucks, it will change way more than that before I get there):

make up to 88k and will only fork out $150 a month = $1,800 a year
88k to 111k you fork out $210 a month = $2,520 a year (additional $720 a year from lower bracket)
111k to 138k you owe $300 a month = $3,600 a year (additional $1,080 a year " " ")
138k to 165k you owe $385 a month = $4,620 a year (additional $1,020 a year " " ")
165k to 500k you owe $475 a month = $5,700 a year (additional $1,080 a year " " ")
500k to Buzz Lightyear (infinity and beyond) you owe $505 a month = $6,060 a year (additional $360 a year) " " "

Depending on where I fall on this chart that Medicare payment being from tax free money can make a an impact on my final outcome if I take out money from my HSA tax free or taxed.  Different topic but another reason to have a ROTH also so you have non-taxable income an can avoid having more taxable income and lower your part B cost.

https://www.kiplinger.com/article/retirement/t039-c001-s003-hsas-can-reimburse-you-for-medicare-premiums-paid.html

Got it, charged just like a regular medical expense, save your tax Medicare payments....

Sorry to piggyback on this but I have a question

I plan on opening a HSA when open enrollment opens later this year. Once I get 1k in the account how does the investing work?

Also lets say I have 10k in it as an example. And I invest 8k of it. Does that mean that 8k is "gone" from the account? If no, does that mean I can withdraw that 8k if needed?

It depends on who administers your HSA. If it is someone like health equity you have two buckets. One for cash, and one for investments. If you have cash you want to invest you just move it to your investment account and buy whatever you want within the plan limits (often they are index funds). If you decide to sell an investment, once it settles the funds are automatically put into your cash account which can take a few days.

Ah gotcha, I will have to look and see who my employer goes though for there HSA

Since everyone is talking up the positives let me just say the decision when you have really good health insurance to then go to a less good plan can be a lot more complex. It's not always a simple a deductible and co pays.  What if the lesser insurer outright denied a massive claim?

I've bounced around the idea myself of going to a lower quality company and plan with work,  but I've been treated really well with current insurance.  $100,000 bills patient owes $0.

Like mentioned before, risk Vs reward.  If you are in good health 87% of the time you might never see the doc except for an annual checkup.  Even in good health you can suddenly end in the ER/hospital due to a car accident or something you did yourself.  Most cases though these claims would be really hard to deny treatment for on the insurance side of the house.  

Say you were a diabetic and needed to be put on a dialysis machine 2-3 times a year and maybe a hospital stay or two.  You would be guaranteed to pay all of your deductible probably before the 1st quarter of the year was over.  Some cases you might be a tax break but that will depend on your income.  If that same person might pay $3600 in deductibles spread out over the year but the HSA guy is going to get hit with his plan amount which currently seems to be around 6-8k depending on the plan (at least the ones I have seen).  I don't think paying an extra 3k a year on medical bills is worth the squeeze when it is all said and done for the HSA guy that has medical issues.  You also have to remember if your married anyone else that is on your policy this also applies to.  Child born with sever asthma or something that requires medical intervention, might not be a good idea depending on how bad it is.

Can you explain more?

Are you talking about deductible, coinsurance & Max OOP?

You need to evaluate your situation to determine if a high deductible plan or a traditional plan makes sense. It comes down to how much medical coverage you actually use. If you or your covered dependents go to the doctor a lot, or need lots of meds, a high deductible plan may not be right for you. If you all are mostly healthy a HDP probably will be cheaper in the long run and give you access to an HSA.

I have a choice of the two plans listed below.  Not sure if either plan will allow an LMSA account as well much less where I can take the money once I hit the minimum required in the account.  The TD ameritrade account deal would be awesome but not my luck.

Back to your question below are the options when I look up my health insurance plans.

The math I see so far for each HSA plan :

Annual Deductible: $1500 in network or $3000 for out of network -(other option)- $2000 for both in and out of network
Medical account contribution: $900 (or) $1200
Net deductible: $600 or $2100 out of network (or) $800
Max out of pocket annual: $5000 or $7000 (or) $6000 or $7500

This is cut and pasted from this article: Health insurance. org but might be better resources for this info

"Well, remember that you’re paying a lower premium for your insurance coverage because it’s a high-deductible plan that doesn’t cover anything other than preventive care before the deductible. If you need to see the doctor, you’ll pay the entire bill (reduced according to the negotiated rates your health plan has with the doctor) if you haven’t yet met your deductible."

What qualifies as preventive care I am not sure to be positive but from my understanding its your basic visits.  Basically the HSA gives you insurance rates at the hospital but you have to pay your deductible first before they pay anything depending on the care you fall under.  On that note the insurance and hospital treatments are a scam.  If you have insurance that 50k visit is negotiated down to 5k when its all said and done.  If you don't have a middle man you get the shaft.

ETA...

This is from Dave Ramsey's website that might help explain what plans fall under the amounts required to have an HSA (you have to have a High Deductible Health Plan / HDHP):

In 2020, that’s a plan with a minimum annual deductible of $1,400 for individuals and $2,800 for families. It also has to have a maximum annual out-of-pocket expense of $6,900 for individuals and $13,800 for families. (An out-of-pocket maximum means the most you’ll pay—on deductibles, copayments, and coinsurance, but not your premium—before your health insurance covers 100% of the remaining balance.)1 If you meet those qualifications, you’re in!

No, I plan on opening a HSA next year. I rarely go see the doctor besides a sinus infection yearly
You have access to two different HSA accounts? Nice!
My employer only has one option for a HSA.

Also question, my HSA option is only $5 cheaper then my Gold option (what I havr currently) does that seem kinda low due to the difference in deductible amount? (Gold is $400, HSA is $1,850)

Oops....really late reply.....

Honestly not sure why you don't get a lower monthly payment but if people are wanting to use an HSA account they probably will make more than the deductible once its all said and done.  I think the difference for me is like $17 a month .  Depending on your income you will save the taxes on the amount of $$$ you put in your HSA account.  The fact that you retain this money and can use it later is a big bonus.  The big fear is getting stuck with a big bill.  If your medical expenses are high the plan may really hurt you.  If there are high enough though it won't matter.  A few years ago I ran into a medical issue that even with your standard medical insurance I had over 6k in payments before the end of the 3rd quarter.  I didn't have to pay a dime once I hit the limit.  All that would mean is that year I would pay all my money in Jan Vs having it spread out over 8 months.  Then I did not receive any tax savings on the amount I could have put in the HSA even though I paid $6k in medical that year.

I would say the best thing to do is make a savings account and say put 1/12th of the max deductible your plan is set for each month.  Do this the year before you start the HSA.  Then in Jan you will have all the money set aside in this savings account for any medical problem that might appear.  Then start a second savings account (or do the math in the first account) and do the same thing.  If you didn't need any of the money come Dec 31st at 11:59pm you then put this money to fund the a ROTH and then some other investment accounts.  This second account is because say you have some medical issue that pops up in Dec and takes your deductible.  When Jan rolls around you still want to have that deductible sitting ready to use for that year.  If your deductible was 7.5k you could in theory pay out 15k within a few days for medical expenses if it happened really late Dec and early Jan.

By max deductible your talking max out of pocket?

@Scoobysmak

See post above

Max out of pocket, I admit not in an HSA so all these numbers are a bit overwhelming and it seems each plan is a bit different on how they charge.  Like in and out of network stuff.  I plan to get in an HSA but like mentioned above only have two options.  So far haven't found how I can control the money in the account in each case.

Over 55 years old you can put in up to $10K per family depending on all the things. I just called my HSA fuckers yesterday.

You can also put in post tax money from a transfer and then get the tax back when you file at the end of the year.  If you have an expense and didn't have enough cash in your HSA, you can add more right up until the tax deadline date.   Phone chick also said I could add/pay myself for any med expenses I had during 2020. I hope this is true.

OP,

If you have VA coverage and you're single, why opt in and pay a premium anyway?

Even though VA healthcare sucks, I chose to just forgo employer sponsored insurance to avoid the cost.  I think when I last looked, there would have been a small advantage to buying into the plan to get access to an HSA, but if I actually used the insurance, the advantage disappeared.

I know when I use the VA, I'm only paying $15 for an in person visit to my PCP.  I pay $50 to see a specialist but it drops to $15 if the PCP orders the visit.

Realistically, it only cost me $50 when I need to do an eye exam.

It did bite me in the ass once when I had to do physical therapy at a private office but that's only because the VA lied to me about my costs and they ended up hitting me with an unexpected bill all at once.  Even then it was only $15 a visit.  IIRC, the total was less than $400 for 2-3 months worth of physical therapy.

A question about HSA's for anyone in the know:  is there an income limit where the contribution is no longer deductible like with an IRA?

I would like to clarify what premium you think I should pay?  

I currently have employer healthcare insurance that I pay for every pay check.  It is just not an HSA currently.  I meet the criteria for VA group 1, now so not sure if I would pay anything for healthcare but still looking into it.  For my service connected stuff its a no brainer and I think for emergency care I think it would be covered but say I  pull a muscle in my back and need either chiropractic care or something else not sure if that is covered.  Still need to find the pit falls since I am a medical nightmare.  

Your situation may well be different from mine but what I am saying is I personally chose to opt out of an employer sponsored health plan, ergo, no premium deducted from my paycheck.  It sounds like that might be a good idea for you, maybe.

I don't recall off the top of my head which group I'm in, but I don't have anything service connected so probably lower than you.  The VA I use has chiropractic care, although I haven't used it.  If your VA facility doesn't you could probably get referred out.  

Speaking of which, if you live a certain distance from a VA facility, you kind of get the best of both worlds because then you get non-VA care (mucho better) at the VA costs.  That's what I did for physical therapy for my back.

If and when I need to see the doctor, I go to the VA.  It cost me a $15 copay to see my primary care provider.  I pay $50 if I need to see a specialist, unless my PCP put in the order for the specialist, then it's $15.  If I do a tele-health visit, it cost me nothing.  Perscriptions are pretty cheap too.

Without health insurance, and thus no HDHP, I don't get the advantage of having an HSA, but I also don't pay any monthly premiums and am still covered through the VA.

Don't get me wrong, VA healthcare sucks.  With a service connected disability, you've probably come to the same conclusion.  It's the definition of socialism.  But, as a veteran, you've earned it.  If it's the best option for you, you might as well make full use of it.

Depending on your healthcare use, tax situation, employer contributions to your HSA, and what your health insurance premiums are, you may be better off opting out of coverage and thus not pay any premium.

I know the VA asks if patients have private health insurance.  I'm not sure how that will affect your costs when using the VA, because as an adult, I've never had health insurance.  It might trigger a deductible if the VA bills your insurance provider for service.  

If not, it may be advantageous to have an employer sponsored health plan with an HSA, grab the "free" employer contribution and the tax deduction, and then get all your healthcare from the VA.  I almost went that route.

So far I have never paid anything but one copay on a medication and that got reimbursed back to me once I pointed out the correct group category should have been under.  It took a few months but I wanted my ducks in a row before I went back to them and prove the error (long story short, it was in the middle of getting my service connection that got denied a few times).  I have at least 6 visits a year for various treatments, they request me to come in and usually schedule me before I leave.  I have a local clinic that I have a doctor but also get sent to the main VA hospital a couple hours away for some of the procedures so I can be a pincushion.  I get blood/piss tested regularly and cancer screenings because of everything that happened.  I have never requested treatment for something like back problems or say a broken arm.  I don't know how that would be handled.  Which for me I would feel safer knowing I wouldn't be forking over 25k for an ER or some other type visit that would have been negotiated down to say 4k just because I have some type of insurance.  

I calculated it will roughly cost me around $300 a year to use/be able to fund an HSA depending on the plan I pick.  This is taking the money that I wasn't taxed on (robbed from uncle sugar) and subtracting the paycheck premium out.  I have now gotten access to the couple of plans and it looks like one of them I can still use an LXFSA (might have the acronym wrong but tax free money for stuff like the extra glasses I get).  I still don't have a clue on what funds I may or may not be allowed to invest in with my HSA money though.

The max donation to an HSA for me being single looks to be $3600 a year.  If I had $6k in my HSA and any year I gained 5% interest on my money I made my $300 back off my investments.  So I predict within 3-4 years I will be making more than my paycheck deductible for having it.  This is calculating for say a 3% year or flat year, if it goes negative then it will be longer.  The bonus if it goes negative when it rebounds I purchased all that at a discount.  In the next 15 years I should be doing much better paying out my $300 a year to keep access to my HSA plan and trying to keep uncle sugar off my payroll.

Overall reducing my taxable income is my goal.  The only reason I never maxed out my FSA account was that I had to use if for specific medical expenses within the year or only a small sliver would transfer to the next year.  Once the VA adopted me I have not had the expenses to use the money in my FSA account without say purchasing 87 million condoms (just kidding, I did buy 3 pair of top of the line glasses though).  

(off topic)
I will say honestly my VA experience on the doctor side of the house has been about the same as I would have found out in town except the first local clinic doctor I got assigned.  As a note: she was not allowed in the building about 6 months after I became her patient.  I made a comment on a sheet but nothing that would have gone to that extent.  Think I said something like, medical knowledge is/was good but had a lack of personality.  My current VA local doc rocks along with my nurse practitioner at the main hospital when I have to travel.  The doctors at the main hospital rotate so one out of 3 gives me a bit of grief but nothing over the top (aka eating out once a week for a cheat meal is bad and I get the frowny face).  The VA really seems to have regional problems, I have had bad luck elsewhere but this is my first full go at it and so far can't complain.

Sounds like paying a premium to get the HSA might be the way to go for you.  I would definitely look into whether or not you could avoid having to pay any deductible by using the VA though, especially if you are happy with your doctors.

When I got out, everything was free (no copay) for the first 5 years.  I think it still would be below a certain income threshold.  Since you're service connected, it wouldn't surprise me if even your non-service connected visits were without a copay or deductible.

I changed doctors not too long ago and am definitely happier with the new guy.  The way they do things is still dumb at times though.  It seems like I have to go through 5 layers of bureaucracy just to talk to someone in my clinic.

My medical record requires a dump truck to move it.....  They fought to keep me alive for almost a year.  I was in the hospital for over 100 days straight.  They placed me right down the hall from the ICU which I had a couple of weeks in as well.  I am much better now but from all the confusion of why all my organs were failing and then realizing why and how bad I was, think they want to keep me as a success story.  Not sure if that is a good thing or a bad thing...  I can text my nurse practitioner at any time, I have her cell phone number along with a 1-800 line to the nurse on call.  

As a note, I started my journey in the civilian world with my issues and they couldn't explain it either.  It only took one test to connect the dots, less than 10% ever need the test to find out what is wrong.  I was transferred to the VA midstream in the all this.  It was less than 5 years from leaving the sandbox when all this went down.  My first symptom's happened less than 2 years from being back but on the non-doctor side of the VA......uh I will just leave this....

Question for you guys

Is there any reason to do paycheck contributions for the whole year or try to max out the HSA as soon as you can?

Wouldn't it be better to max it out ASAP so you have a larger sum to invest/larger returns?

There is no employer match on a HSA so I don't see any point in stretching it out over the year

I would say put it in the entire amount ASAP and wait for a "down day" to buy in at a lower price, I probably wouldn't wait more than a couple weeks though (I might have in 2020 if the news had come out a month earlier).

Many might do it monthly so its more of an automatic thing would be my guess.  I might find out its more of an employer thing since it is tax free money and has to be taken out before taxes unless you claim it on a refund every year.

I stretch mine out over the course of the year, because there is no incentive to do it faster (other than earlier potential market returns) but I like the concept of constant and steady dollar cost averaging over the long term.  Plus, I am front loading my 401k to get the match ASAP which my plan allows, and front loading my Mega Backdoor Roth as soon as I can.  That stretches me really thin as it is.

If I were not stretched thin, I'd probably front load the HSA just to get max contributions in for the sole consideration of a potential job loss, however unlikely.

The most important thing is to max it.  How soon you max it is less important.

Keep in mind if you pretax contributions through your employers 125 plan you also save payroll tax.

Yes, you can contribute post tax and claim the deduction later, but you miss out on the payroll tax savings.