At this point for me, any advice is good advice, so nothing is unwanted.
I've concidered teaching college art, but highschool art is my dream job, as it would give me the chance to make a bigger difference in student's lives. Pluse . . . I've got 3 years toward it already (It will be around 2 years more before I compleate school), and I'm an older student (32, which makes me anxious about transitioning, as, if I understand correctly, the younger you are, the more effective HRT is). I'm kinda at the age where I need to get back into the work force and start a career . . . so the other reason I'm not currently concidering a masters degree to teach art is simply that I want to get back to work as soon as possible.
As for the state I live in . . . it isn't known for its progressiveness. I'm under the impression that government employees are protected from work place discrimination based on gender identity. I'm not sure if that extends to teachers or not, however.