Can I use an HSA to pay financed payments for LASIK?
From HSA Resources -  I understand that I can reimburse myself from my HSA for qualified medical expenses that I pay out-of-pocket but is there a time limit? Do I need to reimburse myself in the same year? You have your entire lifetime to reimburse yourself. As long as you had your HSA established at the time the expense was incurred, you save the receipt and it was not otherwise reimbursed, you can reimburse yourself for the expense from your HSA even years later. The important thing not asked or mentioned above is that the HSA must be in place before the expense occurred. In your case, should the LASIK procedure be before the HSA is established, it's not an eligible expense.
There is no need to get an auto loan just to try and affect your credit score. It is possible to have a score over 800 without any sort of auto loan. If you can afford to pay for the vehicle up front that is the better option. Even with special financing incentives it is better to pay up front if you can. Yes it is possible to use the funds to make more if you finance with a silly low interest rate, however it's also possible to lose a job or have some other financial disaster happen and need that money for something else making it more difficult to make the payment.  It may be just me but I find the peace of mind not having the payment to be worth a lot. I work in the FSA/HSA/HRA industry and just wanted to point out that if your wife has a medical FSA, you cannot contribute to an HSA whether or not you are covered by her medical insurance plan. The only exception to this per the rules is if your wife's employers plan limits the medical FSA benefit to the employee, your wife, which I can say from experience is extremely rare. It's possible, but I've never personally seen an employer with this in their plan document, so better check first to be sure the FSA is restricted to your wife only. You have to understand the FSA to know why this is true. Unless restricted, your wife can use her medical FSA for herself, her spouse, and any tax dependents. Meaning whether or not she uses the FSA for your eligible expenses you still have 1st dollar coverage from the FSA, making you in-eligible to open and contribute to an HSA until the end of the plan year and possibly grace period if her employer has one in place and she does not spend her funds by the end of the plan year. Hope this helps. If your still not sure, talk to a tax professional, which I am not, but do advise employers and participants on both HSAs and FSAs. You can negotiate a no penalty for early payment loan with dealerships sometimes. Dealerships will often give you a better price on the car when you finance through them vs paying cash, so you negotiate in a 48 month finance, after you've settled on the price THEN you negotiate the no penalty for early payment point. They'll be less likely to try to raise the price after you've already come to an agreement.  My dad has SAID he does this when buying cars, but that could just be hearsay and bravado. Has said he will negotiate on the basis of a long term lease, nail down a price then throw that clause in, then pay the car off in the first payment.  Disclaimer: it's...um not a great way to do business though if you plan to purchase a new car every 2-3 years from the same dealer. Do it once and you'll have a note in their CRM not to either a) offer price reductions for financing or b) offer no penalty early payment financing. If you can afford to max out an HSA and cover out of pocket expenses without withdrawing from it, it makes sense to do so.  It might sound initially risky to tie too much money to healthcare expenses, perhaps you'll enjoy exceptional health and not need those funds. However, the annual contribution limit ($3,350/year for an individual) is low enough that it's unlikely you'd overfund your HSA, but even if you didn't need it all for healthcare, after 65 you can withdraw HSA funds without the 20% withdrawal penalty that you're hit with if under 65, so best case it's tax-free, worst-case it's like an IRA.  From a tax perspective, your contributions are a tax-deduction like a traditional IRA, there's no tax on the gains, and you withdraw it tax-free as well, so long as you have healthcare expenses. The tricky bit is you can get reimbursed for your expenses at any time. If you pay out of pocket now, in 20 years you can get a reimbursement from your HSA: From HSA Bank's FAQ Can I use my tax-free HSA savings to pay for — or reimburse myself for   — IRS-qualified medical expenses from a previous year?    Yes, as long as   the IRS-qualified medical expenses were incurred after your HSA was   established, you can pay them or reimburse yourself with HSA funds at   any time. Just be sure to keep sufficient records to show that these   expenses were not previously paid for by another source or taken as an   itemized deduction in any prior tax year. I was in your situation a few years ago and I discovered something that worked perfectly for me - a local health insurance broker. I met with her, discussed my needs, reviewed the options with her, then acted. She received a commission from the insurer, so it cost me nothing. I would certainly follow a similar approach again. Wells Fargo offers to rollover existing HSA accounts without mentioning the need to be changing plans, jobs, or providers so I don't think you need a life event to make the switch but you can check with your new provider to make sure prior to opening the account. Like most things HSA-related the rules for rollovers are probably similar to the rules for an IRA but once again your best bet is to check with your new provider. HSA Administrators allows you to invest in a large variety of Vanguard funds and were the best I found for investing when I was looking. "I am very late to this forum and post - but will just respond that I am a sole proprietor, who was just audited by the IRS for 2009, and this is one of the items that they disallowed.  My husband lost his job in 2008, I was unable to get health insurance on my own due to pre-existing ( not) conditions and so we had to stay on the Cobra system.  None of the cost was funded by the employer and so I took it as a SE HI deduction on Line 29.  It was disallowed and unfortunately, due to AGI limits, I get nothing by taking it on Sch. A.  The auditor made it very clear that if the plan was not in my name, or the company's name, I could not take the deduction above the line.  In his words, ""it's not fair, but it is the law!""" "According to the instructions for IRS Form 8889,  Expenses incurred before you establish your HSA are not qualified medical expenses. If, under the last-month rule, you are considered to be an eligible individual for the entire year for determining the contribution amount, only those expenses incurred after you actually establish your HSA are qualified medical expenses. Accordingly, your medical expenses from year A are not considered ""qualified medical expenses"" and you should not use funds in your HSA to pay them unless you would like to pay taxes on the distributed funds and a 20% penalty. Publication 969 states very clearly on page 9: How you report your distributions depends on whether or not you use the distribution for qualified medical expenses (defined earlier). If you use a distribution from your HSA for qualified medical expenses, you do not pay tax on the distribution but you have to report the distribution on Form 8889. There is nothing about the timing of contributions versus distributions. As long as the distribution is for a qualified medical expense, the distribution will not be included in gross income and not subject to penalty regardless of how much money you had in your HSA when you incurred the medical expense."