Financed medical expenses and tax deductions
You deduct expenses when you incur them (when you pay the hospital, for example). Medical expenses are deducted on Schedule A, subject to 7.5% AGI threshold. Financed or not - doesn't matter. The medical expense is deductible (if it is medically necessary), the loan interest is not.
"To be deductible, a business expense must be both ordinary and necessary. An ordinary expense is one that is common and accepted in your trade or business. A necessary expense is one that is helpful and appropriate for your trade or business. An expense does not have to be indispensable to be considered necessary.  (IRS, Deducting Business Expenses) It seems to me you'd have a hard time convincing an auditor that this is the case.  Since business don't commonly own cars for the sole purpose of housing $25 computers, you'd have trouble with the ""ordinary"" test.  And since there are lots of other ways to house a computer other than a car, ""necessary"" seems problematic also." I fell into a similar situation as you.  I spent a lot of time trying to understand this, and the instructions leave a lot to be desired.  What follows is my ultimate decisions, and my rationale.  My taxes have already been filed, so I will let you know if I get audited! 1.)  So in cases like this I try to understand the intent.  In this case section III is trying to understand if pre-tax money was added to your HSA that you were not entitled too.  As you describe, this does not apply to you.  I would think you should be ok not including section III (I didn't.) HOWEVER, I am not a tax-lawyer or even a lawyer!   2.) I do not believe these are medical distributions From the 8889 doc....   Qualified HSA distribution.   This is a distribution from a health flexible spending arrangement (FSA) or health reimbursement arrangement (HRA) that is contributed by your employer directly to your HSA. This is a one-time distribution from any of these arrangements. The distribution is treated as a rollover contribution to the HSA and is subject to the testing period rules shown below. See Pub. 969 for more information.   So I don't think you have anything to report here.   3.) As you have no excess this line can just be zero.   4.) From the 8889 doc This is a distribution from your traditional IRA or Roth IRA to your HSA in a direct trustee-to-trustee transfer.   Again, I don't think this applies to you so you can enter zero. 5.) This one is the easiest.  You can always get this money tax free if you use it for qualified medical expenses. From the 8889   Distributions from an HSA used exclusively to pay qualified medical expenses of the account beneficiary, spouse, or dependents are excludable from gross income. (See the line 15 instructions for information on medical expenses of dependents not claimed on your return.) You can receive distributions from an HSA even if you are not currently eligible to have contributions made to the HSA. However, any part of a distribution not used to pay qualified medical expenses is includible in gross income and is subject to an additional 20% tax unless an exception applies.   I hope this helps! A medical expense is only a qualified medical expense eligible for an HSA distribution if it is not reimbursed by insurance.  If you know that you will be reimbursed, do not pay for it through your HSA. Think of it this way: you can only be reimbursed for a medical expense once.  Either you get reimbursed by your insurance, or you get reimbursed by your HSA, but not both. If you pay for the expense with your HSA and are later reimbursed, you need to return the money to your HSA through a mistaken distribution repayment.  This is not considered a contribution, but you need to make sure to tell your HSA provider that it is a mistaken distribution repayment and not a contribution, so that it gets accounted for correctly. During World War II, the United States (US) instituted wage and price controls.  To attract better employees, companies would offer benefits to get around salary limits.  Health insurance was one of the more successful benefits.   At that time, income taxes were newer and there were many ways to evade them.  Companies could generally deduct expenses.  So at that time, health care was deductible because everything was.  And at that time, only wages were taxable compensation from employer to employee.   Since that time, many other benefits have become non-deductible for employers, e.g. housing or the reduced deduction for meals and entertainment.  But health care is generally regarded as different, as a necessity.  While everyone needs to eat, not everyone needs to eat at a $100 a meal restaurant.  People who need expensive health care really need it.  People who eat expensive food just prefer it.   And of course, health care is more intermittent where food is relatively consistent.  You don't need ten thousand calories one day and zero the next.  But some families have no health care expenses in a year while another might have cancer or a pregnancy.  Note that medical care expenses can be deducted for individuals if they are large enough in aggregate and you itemize.   And of course both businesses and workers have incentives to maintain the current system with deductibility.  Health insurance is a common benefit.  Housing is not (although it's worth noting that travel housing and meals are deductible).  So there have been few people impacted by making housing taxable while many people would be impacted by taxable health insurance.   You can deduct health insurance costs if self-employed.  It's also not true that health insurance is the only benefit with preferential tax treatment.  Retirement and child care are also deductible.  Even meals and housing can be deducted in certain circumstances.  The complex rules about what and how much is deductible.   There have been rumbles about normalizing the tax treatment of health insurance and medical care, but there is a lot of opposition.  Insurance companies oppose making all healthcare expenses deductible, as that reduces their effective benefit.  They would prefer only insurance premiums be deductible.  Traditionally employed individuals oppose making health insurance taxable, as that would increase their taxes.  So the situation persists.  There isn't quite enough support to move in either direction, although the current compromise is economically silly. It appears that this is the case.  From IRS Publication 969, Health Savings Accounts and Other Tax-Favored Health Plans Qualified medical expenses are those incurred by the following persons. You and your spouse. All dependents you claim on your tax return. Any person you could have claimed as a dependent on your return except that: The person filed a joint return, The person had gross income of $3,700 or more, or You, or your spouse if filing jointly, could be claimed as a dependent on someone else's 2011 return. I've considered just calling the out-of-network hospital and asking   them to reduce the charges. Ideally they would send my health   insurance provider a smaller bill which I could just pay. However I   want to be careful about how I proceed. Yes, that's what you should be doing. They might give you a discount, but even if not - they will definitely be willing to work out a payment plan for you so that you could pay in installments and not in a lump sum. I have experience with the El Camino group in California, that did just that. It was several hundreds, so they didn't give a discount, but were able to work out an installment plan for several months without much hassle. That is something to do before you get to lawyers. I'm not sure I know how the lawyer could be useful to you, other than claiming bankruptcy or waiting for them to turn to collections and then fight those. You should also work with your insurance. How much is your deductible? If your deductible is so high that it exceeds the several thousands bill you got - do you have a HSA? FSA? These will allow you paying the bill with pre-tax money, saving quite a lot (depending on your brackets and how much you put there). I would expect the insurance to bill you for the deductible, and cover all the rest. Is it not what is happening? No, you cannot. You can only deduct expenses that the employer required from you, are used solely for the employer's (not your!) benefit, you were not reimbursed for them and they're above the 2% AGI threshold. And that - only if you're itemizing your deductions. I'm not an expert, but here's my $0.02. Deductions for business expenses are subject to the 2% rule. In other words, you can only deduct that which exceeds 2% of your AGI (Adjusted Gross Income). For example, say you have an AGI of $50,000, and you buy a laptop that costs $800. You won't get a write-off from that, because 2% of $50,000 is $1,000, and you can only deduct business-related expenses in excess of that $1,000. If you have an AGI of $50,000 and buy a $2,000 laptop, you can deduct a maximum of $1,000 ($2,000 minus 2% of $50,000 is $2,000 - $1,000 = $1,000). Additionally, you can write off the laptop only to the extent that you use it for business. So in other words, if you have an AGI of $50,000 and buy that $2,000 laptop, but only use it 50% for business, you can only write off $500. Theoretically, they can ask for verification of the business use of your laptop. A log or a diary would be what I would provide, but I'm not an IRS agent. "You should probably have a tax professional help you with that (generally advisable when doing corporation returns, even if its a small S corp with a single shareholder). Some of it may be deductible, depending on the tax-exemption status of the recipients. Some may be deductible as business expenses. To address Chris's comment: Generally you can deduct as a business on your 1120S anything that is necessary and ordinary for your business. Charitable deductions flow through to your personal 1040, so Colin's reference to pub 526 is the right place to look at (if it was a C-corp, it might be different).  Advertisement costs is a necessary and ordinary expense for any business, but you need to look at the essence of the transaction. Did you expect the sponsorship to provide you any new clients? Did you anticipate additional exposure to the potential customers? Was the investment (80 hours of your work) similar to the costs of paid advertisement for the same audience? If so - it is probably a business expense. While you can't deduct the time on its own, you can deduct the salary you paid yourself for working on this, materials, attributed depreciation, etc. If you can't justify it as advertisement, then its a donation, and then you cannot deduct it (because you did receive something in return). It might not be allowed as a business expense, and you might be required to consider it as ""personal use"", i.e.: salary." As the answer from Guest5 noted, any expense you have before the HSA is established is not considered a qualified medical expense for an HSA distribution. However, it is important to note that since you now have the HSA established, any medical expense you have from this point on is a qualified medical expense, even if you don't take an HSA distribution for it right away. For example, let's say that you have a medical expense this year, but you don't take an HSA distribution to reimburse yourself right away.  (Maybe it is because you don't have enough money in your HSA to reimburse yourself at this time.)  You can reimburse yourself in the future for this expense.  As long as you had an HSA in place when the expense was incurred, it doesn't matter if you wait to take the distribution. "While COBRA premiums are not eligible to be a ""business"" expense they can be a medical expense for personal deduction purposes.  If you're itemizing your deductions you may be able to deduct that way.  However, you will only be able to deduct the portion of the premium that exceeds 10% of your AGI. Are you a full time employee now or are you a 1099 contractor?  Do you have access to your employers health plan?" "You can deduct what you pay for your own and your family's health insurance regardless of whether it is subsidized by your employer or not, as well  as all other medical and dental expenses for your family, as an itemized deduction on Schedule A of Form 1040, but only to the extent that the  total exceeds 7.5% of your Adjusted Gross Income (AGI) (10% on tax returns for year 2013 onwards). As pointed out in KeithB's comment, you cannot deduct any health insurance premium (or other medical expense) that was paid for out of pre-tax dollars, nor indeed can you deduct any medical expense to the extent that  it was paid for by the insurance company directly to hospital or doctor (or reimbursed to you) for a covered expense; e.g. if the insurance company reimbursed you $72 for a claim for a doctor's visit for which you paid $100 to the doctor, only $28 goes on Schedule A to be added to the amount that you will be comparing to the 7.5% of AGI threshold, and the $72 is not income to you that needs to be reported on Form 1040. Depending on other items on Schedule A, your total itemized deductions might not exceed the standard deduction, in which case you will likely choose to use the standard deduction. In this case, you ""lose"" the deduction for medical expenses as well as all other expenses deductible on Schedule A. Summary of some of the discussions in the comments   Health care insurance premiums cannot be paid for   from HSA accounts (IRS Pub 969, page 8, column 2, near   the bottom) though there are some exceptions.  Nor   can health care insurance premiums be paid from an   FSA account (IRS Pub 969, page 17, column 1, near the top). If you have a business on the side and file a Schedule C as a self-employed person, you can buy medical insurance for that business's employees (and their families too, if you like) as an employment benefit, and pay for it out of the income of the Schedule C business, (thus saving on taxes). But be aware that if you have employees other than yourself in the side business, they would need to be covered by the same policy too.  You can even decide to pay all medical expenses of your employees and their families too (no 7.5% limitation there!) as an employment benefit but again, you cannot discriminate against other employees (if any) of the Schedule C business in this matter.  Of course, all this money that reduced your Schedule C income does not go on Schedule A at all. If your employer permits your family to be covered under its health insurance plan (for a cost, of course), check whether you are allowed to pay for the insurance with pre-tax dollars.  The private (non-Schedule C) insurance would, of course, be paid for with post-tax dollars.  I would doubt that  you would be able to save enough money on taxes to make up the difference between $1330/month and $600/month, but it might also be that the private insurance policy covers a lot less than your employer's policy does.  As a rule of thumb, group insurance through an employer can be expected to offer better coverage than privately purchased insurance. Whether the added coverage is worth the additional cost is a  different matter.  But while considering this matter, keep in mind that privately purchased insurance is not  always guaranteed to be renewable, and a company might decline to renew a policy if there were a large number of claims. A replacement policy might not cover pre-existing conditions for some time (six months? a year?) or maybe even permanently.  So, do consider these aspects as well.  Of course, an employer can also change health insurance plans or drop them entirely as an employment benefit (or you might quit and go work for a different company), but as long as the employer's health plan is in existence, you (and continuing members of your family) cannot be discriminated against and denied coverage under the employer's plan." "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." There is no distribution limit.  Even if you distributed more than your medical expenses, the excess would be taxed and penalized, but it would still be distributed, and the penalty would be based on the amount that wasn't for medical expenses, regardless of the total amount. My brother's wife does some pretty intense couponing. She recently posted on facebook when she bought about $300 worth of items for $30. It was almost all toiletries and food that her family uses regularly, though there were some items they've now got 3 months supply of. She told me that it is a pain to track and exploit all of the different coupons/discounts but the savings help to offset the cost of homeschooling 4 children.