Well you can call the 800-829-1040 line and ask them for help but don't be surprised if you get the wrong answers.  I recently had one rep tell me to go to H.R. Block if I needed help with doing my taxes.  I managed to get it all done without the help of anyone but myself, thank goodness.  This can be a very stressful time for some of us.  I don't itemize so I don't have to fool with all that aggravation of adding up all the medical and see if it is over a percentage of total income before it can be deducted.  Just to make sure you know "I HATE doing taxes" too!!

I hate doing taxes too!!  No hope for me getting it done by Sunday.  I have some ETFs, and they don't have to finalize their statements until 60 days after the end of their fiscal year, so that's often at least 60 days after Jan 30 - I haven't gotten those statements yet, so I'm trying to calculate them.  Itemization is the pits, and I have an FSA (health care spending account), so I'll have to get that together too.  I'll probably have to file an extension for my federal and state, but I can't for my FSA.  I'd better give that more priority.

Thanks for this thread so I can remember to do that because I can't get an extension for my FSA.

I hate, hate, hate doing my taxes.  Did I mention I hate doing my taxes? I really hate doing my taxes.  NJ

Good work, cookiegal!  Give yourself a reward!  I got my stocks part done, now to the medical.

turbo tax ! 

I buy this every year ... easier than crunching the numbers on a calculator AND it asks the questions that point out new items.  Medical expenses are the pits -- only reason i was ever able to deduct was that I also have Long-term care insurance premiums ... and reduced income the year I was off work.  Don't forget parking / mileage expenses for going to doctor visits and treatments.

The night before last I painstakingly went through all my medical bills, Rx receipts and I calculated mileage for all doctors' visits in 2010. I used to use TurboTax, but last year I used the free tax help at the local library. I went back to them again yesterday and they did my taxes for me, filed electronically too. After all my hard work, I found that it wasn't worthwhile itemizing my deductions and took the standard deduction instead. But at least I now have all my medical bills in a nice neat pile.

For me, once I have figured out our medical expenses, doing the taxes is a breeze. Over the years, I have developed a system that works. I keep an electronic calendar that gives every appointment (good for mileage and to make sure nothing is forgotten). For frequently visited doctors, I get a list of all of the appointments for the year from the office. I also create a spreadsheet for mileage, tolls, etc for all frequently visited places.

As I get receipts, I throw them in a file. Every couple of months, I tape each receipt on its own piece of paper and organize them by date. I glance at insurance EOB's as they come in. If I don't find any big problems, I stick them in a different file. At the end of the year, I go through our bank statements, credit card statements and the medical calendar. I then enter all of the expenses into an excel spreadsheet. Like amontro, I have a column for all expenses, and then each expense is listed in a column by types (e.g., doctor, RX, travel, DME, etc. Once the spread sheet is done, I go through insurance EOBs to see what, if anything, was covered. Once everything is "right" in the spreadsheet, I organize all of the receipts by date, and make scans.

When deciding whether or not to document medical expenses for tax purposes, check what your state guidelines are. Fed taxes require medical expenses to exceed 7.5% of income, but some states have much lower thresholds. It's a pain in the butt, but last year we saved thousands of dollars by itemizing medical expenses. I hate hate hate documenting all of this stuff, not just because of the time and effort, but because it reminds me of medical things that I had forgotten. - KS

PS If you do itemize keep every little scrap of paper. Also, there has been a change in the law that means over the counter things like calcium are no longer deductible UNLESS you get a letter of medical necessity from your doc.

Thanks, JBinOK!  That's very good to know if I have to do this again.