I hate to add to your list of things to do, but you should also have either a birth certificate or a passport with an M. If you ever need a BC, a passport is almost always (I'm tempted to say "always") an acceptable substitute.
The way I understand it, you most certainly will have trouble with your FAFSA if the SSA has you as female. So I would take care of Social Security pronto.
The medical issue is tricky. Even if you don't consider trans* a medical condition, the fact still remains that you are on medication for that condition. You will have to list your high blood pressure, though, right? What if you describe trans as a hormonal deficiency or something like that? I would actually talk to the doctor and see what he or she says--find out how to describe your condition, without outing yourself, in a medically acceptable way.
P.S. Privacy laws dictate that the school cannot call your doctor and ask questions about your history. Is self-disclosure all the school is asking for?
