Before you read this, you should know I'm 18, going on 19 in about 1 month.

Currently, I've been seeing a gender therapist for the past 5 or 6 months, but I've been seeing therapists all over my state for the past 2.5 years. I'm due. My current therapist, the only true GT, refuses to get my HRT letter until I: Get a job, become more socially active, and "cross live" for 3 months.
Okay, I have no problems with the job business, but the problem is, this incorrect gender role is holding me back, at least on a personal level. I live in tiny area where everybody knows somebody who knows YOU. As a result, I find it downright impossible to work as anyone but who I really am. It will get back to me, my college, and eventually a future employer. I might sound paranoid, but my state is so small that I would be more surprised if this didn't happen than if it did.
For being more social, my concerns are similar: Too many people know each other around here. I'd rather tell a potential friend during transition, rather than now. Yes, if they are real friends, they'd stick with me, however, to the general populace (in a non-dating/relationship context), it looks easier to say that "I had/have a male body, but that's not who I am" as opposed to "I am a girl, despite that fact that I have a bass voice and look like a guy." I plan to get into some local support groups in a couple of weeks after my finals are finished, so hopefully that will help.
On the 3rd issue, cross-living for 3 months: This has me livid. He says this is according to SOC. That's fine, I have zero issues with the SOC. My issues are this: He treats the SOC as laws of the world, and must be enforced. As I said before, his facts, upon self-research are somewhat incorrect: It can be 3 months of RLE, as he said.
Or, it can be 3+ months of therapy. I've had 27 months, which is certainly "at least 3." I can NOT pass right now, despite being only 18; I've been cursed with the lowest male voice I have ever heard or seen performed.
I am also concerned with his very frequent talks about sex. He asks what I think about during fantasies. This is also his specialty, he has written a few ED books over the years. Still, I don't care- that's my business and has nothing to do with my gender identity. He also seems to think that I won't get a job, friends, etc. until after surgery; I have no idea why, I have never said anything of that nature.
My plan is ideally: Start HRT soon (like, this month or next), start my sophomore year as me, and get a job then! I don't see the issue with this, it's pretty much reasonable.
Any ideas for me? Despite having 35+ years in the field, is he a good GT for me? I admit I need a lot of better work and social skills, but what should I bring up with him during my next session?