While I would never want any troubles from the IRS, I don't hesitate to claim every legal and substantiated deduction I'm entitled to. Yes, it will look odd, but assuming he has all the documentation, he should claim everything. Don't forget things like mileage for driving back and forth to doctors and hospitals, over the counter purchases, etc. There are quite a few things that fall under medical expenses which no one cares about unless (like your friend) you can get over the 7.5% limitation.
If they question it, it's very likely he'll only need to mail in copies of his receipts, and that will be the end of it. Most times when the IRS questions something, they ask only for documentation of the specific item they are questioning. So it doesn't make sense to not claim things in other areas if you are entitled.
Claim only what you can document.