I used TurboTax online, and it walked me through everything. I deducted my top surgery, endo fees, all prescriptions, dental, eye exam and glasses, and dr. office co-pays. Since my insurance is through my employer, I could not deduct health insurance premiums (they are pre-tax). All that added up to around 8k, and I only got back about $1300 more than last year. The endo and top surgery were not covered by my insurance at all. I should also note I bought a new car and got to deduct the large ad valorem tax charged by my state, so I'm sure that added a chunk to my refund aside from the medical deductions.

I could only write off what I had receipts for, or it would have been more. I put top surgery on my credit card, so I was able to write it off for 2014, even though I haven't paid off the card balance (yet).