Hey, Gnomekid, let me see if I can be of some help.
You made a comment about looking to see what insurance company offers this benefit. I don't believe that any of the insurance companies through the Obama Exchange offers gender surgeries (or at least they don't HAVE to by law...worth looking into I think). Medicaid (all states) do not cover gender surgeries. If you aren't getting your insurance through the exchange, or through the State, you will have whatever insurance your employer offers.
I wouldn't suggest picking a job based on what insurance they offer their employees. You most likely won't be able to find out if their insurance package covers gender surgeries before taking the job. Additionally, employers jump from one insurance company to the next, so even if you knew for sure their plan covered the surgery when you were hired, you may not even be able to get the surgery before they change their insurance plan yet again (companies renew plans once per year).
Like I said in an earlier post, Aetna and Cigna seem to be the only two insurance companies to my knowledge that will cover gender surgeries. However, your specific company has to choose to have that as a part of their package. You and your friend could both have Aetna, but his company's insurance policy will pay for gender surgeries, while yours doesn't.
My experience is that there are two types of companies who will pay for this "benefit" for their employee.
Companies who want to "look good" and non-profits who actually give a ->-bleeped-<-.
It is very possible your father's high end company won't pay, while one's theater company will.
It is the luck of the draw, my friend.
Your best bet would be after you get your first job and the company
doesn't have the benefit, start fighting to get it written into the next year's policy.