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.
You're right. That's pretty much it. You get a deduction for any medical expenses above 10% of your Adjusted Gross Income. You also have to itemize your deductions; claiming the standard deduction won't do. Some of the expenses you describe may be eligible to be paid off by a 401(k) without incurring a penalty. As long as you do not mind paying tax on the extra income. If your tax bracket does not go up, then using your IRA may not be a bad idea. You should consult a tax expert and see which expenses can qualify for a withdrawal without penalty.  I believe medical bills and medical insurance costs are eligible to be withdrawn without penalty in some instances. Here are the advantages to the HDHP/HSA option over the PPO option, some of which you've already mentioned: Lower premiums, saving $240 annually. Your employer is contributing $1500 to your HSA.  As you mentioned, this covers your deductible if you need it, and if you don't, the $1500 is yours to keep inside your HSA. The ability to contribute more to your HSA.  You will be able to contribute additional funds to your HSA and take a tax deduction. Besides the medical expenses applied to your deductible, HSA funds can be spent on medical expenses that are not covered by your insurance, such as dental, vision, chiropractic, etc.  Anything left in your HSA at age 65 can be withdrawn just like with a traditional IRA, with tax due (but no penalty) on anything not spent on medical expenses. With the information that you've provided about your two options, I can't think of any scenario where you'd be better off with the PPO.  However, you definitely want to look at all the rest of the details to ensure that it is indeed the same coverage between the two options.  If you find differences, I wrote an answer on another question that walks you through comparing insurance options under different scenarios. So long as you don't hate what you are doing, I'd say the price is somewhere in the neighborhood of $100-200 year of income to be worth the bookkeeping. I'd only say more than that if you have a ridiculously complex tax situation, you have an irrational hatred of filling out a few forms once a year, or if you just have such a stupidly large amount of money that even having a few hundred dollars a year to donate to people in desperate need just doesn't mean anything to you. Or if you are under special income limits and just a few dollars of income would put you in a bad situation (like a loss of medical benefits, etc). The reason is actually quite simple: the taxes aren't really that hard or time consuming. I've handled three self-employment businesses in my life, and unless you are trying to itemize every last dollar of business deductions and expenses, or you really want to scrape out every last cent from minor deductions that require considerable extra paperwork, it's a few extra forms on your taxes. Most of the extra taxes are as a percentage, so it reduces the benefits, but really not by much. You don't have to make it extra complicated if the extra complexity doesn't give you a big payoff in benefit. I would suggest you pick the simplest imaginable possible system for accounting for this, so that you might only spend an extra few hours per year on the books and taxes. Don't keep $10 sheet music receipts if you feel it's a burden to try to itemize expenses, etc. Instead, the decision should be if you (or in this case your wife) would enjoy doing it, and bringing in money can just be nice in it's own way. I'd suggest she keep some out for little extra niceties, earmark some for feel-good charitable giving, and then of course sock away the rest. Don't let extra income be an unnecessary burden that prevents you from getting it in the first place. "See this question regarding the relationship between a HDHP (High Deductible Health Plan) and an HSA (Health Savings Account). In brief, to qualify for an HSA you must have a HDHP: HDHPs are plans with a minimum deductible of $1,200 for self-only coverage and $2,400 for self-and-family coverage. The maximum amount out-of-pocket limit for HDHPs is $5,950 for self-only coverage and $11,900 for self-and-family coverage. As mentioned by Stainsor, your insurance can either come from your employer, or it can be an individually purchased plan. The HSA can be bundled as part of a package with the insurance, or it can be an account you set up separately. Contributions you make to the HSA are tax deductible. You'll report the amount you contributed when you file your taxes the following year. E.g. in April 2012 you'll report (and deduct) the amount of HSA contributions you made for tax year 2011. I'm not sure what kind of trouble you'll get into if you have an HSA without having a qualified HDHP. To answer the main part of your question: Different HSAs may have slightly different features, but I've typically seen them provide the following ways to withdraw funds: Via a debit card issued with the account. You can use the debit card to pay for things like drugs at the pharmacy, or at a doctors' office that requires payment at the time of service. Via online bill pay. You can use this to pay bills from hospitals, doctors' offices, or other healthcare service providers that send you bills. Via paper checks. For doctors' offices that require payment at time of service but don't accept plastic. (Or if you prefer not to use online bill pay.) Via withdrawal at a teller window or ATM. You can use this to ""reimburse yourself"" for healthcare expenses that you paid out of pocket. The issue of documenting legitimate expenses and/or qualifying for the account with an HDHP is between you and the IRS. The bank at which your HSA is kept doesn't really care whether you comply with the tax laws." "The piece is a little misguided at best and poor journalism at worst. The problem lies in the difference between what's deductible for individuals and what's deductible for corporations. The short version of the story is that corporations can deduct a hell of a lot more things than individuals can. Individual deductions are spelled out in the Internal Revenue Code. Stuff like medical expenses (above 7.5% of your AGI), certain educational things, etc.  For corporations, the basic rule is that they can deduct any ""ordinary and necessary"" business expenses. That includes operating, travel, interest, employee, etc.  I wish that the article had cited specific sections of the Code if this was some kind of loophole or something, but alas, it appears that they didn't. That leads me to believe that these companies are deducting the portion not paid to the government as a business expense.   ~~For what it's worth, I don't believe that a company can deduct those expenses for tax purposes unless it's to ""protect their business interests."" My assumption (I don't have the time or desire to search case law right now) is that settlements with the US Government are considered to fall under that definition.~~  **EDIT** - See my comment [here](http://www.reddit.com/r/business/comments/11dbzu/federal_regulators_have_lauded_a_series_of/c6ll7ez) for the relevant Treasury Regulation dealing with this." An important risk is that the government may decide to change the rules. For example, prior to 2011, over the counter drugs like aspirin, Tylenol, Nyquil, etc. were eligible expenses. You could use your HSA money to buy as much as you wanted. Beginning in 2011, those rules changed. Now, if you want to spend your HSA money on Tylenol, you need a prescription for it. The value of HSA dollars was diminished in the sense that the universe of eligible expenses was diminished. No one knows what the HSA rules will be in the future. What will be eligible expenses? Who will be eligible providers? What kind of compliance paperwork will be required? What kind of fees will be imposed? Personally, I'm a great believer in HSAs. I've saved in one for years. But remember that the government makes the rules regarding their use. They've changed the rules to the detriment of HSA owners at least once; I won't be surprised if it continues. You should check several things: How your business can deduct your child care expenses is beyond me. If your mother-in-law starts a business as a neighborhood babysitter, she might get some deductions for her related expenses though.