Well, as far as question 1, one of our biggest hurdles, I think, is to get over feeling like a freak. And that one can sneak up on you. I was feeling very good about myself through most of my early transition, including going full-time in April (with only 3 weeks of HRT under my belt at the time), but in late summer, I tried my hand at Internet dating, and realized that I was thinking that anyone who would find me attractive/desirable (in my current configuration) would have to be SICK, which tipped me off I was still thinking of myself as "freak", and practicing self-hatred. That jolted me into awareness, and (with my therapist's help) I finally broke (mostly) free of that. And I had a couple of short flings with "nice/normal" men, which showed me the error of my thinking!
As for Question 2, I came to realize that a Gay guy won't treat you as a woman, he's into guys. So... if you want a man, don't try to make it with a gay guy, go for someone who's bi at least (IMHO, YMMV).
