I'm more concerned about documenting things like transportation costs, mileage, etc. Is an Excel spreadsheet OK for documenting these expenses? I hope so, because that's what I use. Just make sure you keep some sort of contemporaneous record. My spreadsheet has three columns for medical: Co-pays, Miles, and Misc. Out of Pocket (tolls, public transit, parking, etc.) I assume I need a receipt every time I need to take a taxi, if I'm not able to drive myself? What about parking fees? The medical center does not give receipts for parking fees (I've asked). These are small amounts ($3 for parking, maybe $10 for taxi fares) but they do add up.Get receipts when you can, but claim cash payments even if you can't get a receipt. (Note to lurkers: This doesn NOT apply to charitable contributions.) I once asked an auditor what she did about cash without a receipt Schedule A deductions. She told me she saved them for last, by which time she knew whether she was dealing with an honest person or not.This is a more obscure question, but if I buy a software program to track my diabetes testing results, would that be deductible? I didn't see that in 502.I would think so. BTW, if you're new to the diabetes world, you might want to check out the Fool's board: http://boards.fool.com/diabetic-fools-116266.aspxPhilRule Your Retirement Home Fool
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