I stopped by the career services office at my college, today, to see if they might by some off chance have any transgender resources. They didn't have much, but they were astonishingly understanding and did have one rather brilliant suggestion:
One of my biggest concerns is that my preferred name (soon to be my legal name) is generally considered to be a "female" name, even though I present as an androgynous guy. Well, apparently it isn't unheard of for people with ambiguous/confusingly gendered names (i.e. women named "Aaron" instead of "Erin" or men named "Ashley") to prefix their name with their title (Mr./Ms./etc.) on resumes and cover letters to prevent confusion. I do believe I could get away with listing myself as "Mr. Diane..." on my resume to indicate that yes, I am a guy and yes, my name is Diane. Weird names happen-- most employers are aware of this.
Additionally, it appears I'm going to get to test this theory soon, not necessarily with resumes, but with describing myself as "Mr." in a professional context. I was feeling optomistic on my way home from the career services office, so I stopped by the education department to talk to my academic advisor (who has been rather unhelpful in the past, but we won't get into that)-- I wasn't expecting much, but after talking in circles for a bit, to my surprise... he informed me that I am completely allowed to present as (an androgynous) male and introduce myself as "Mr." for my teaching field experiences!
Sounds like I'm going to be able to start presenting as myself while teaching sooner than I expected! Thank heavens-- I was kind of afraid I wouldn't have the opportunity until after I graduate and start actually teaching, which would be pretty scary territory to venture into straight out of college and in my first major career. Of course, it's still nervewracking even as a student, especially since I'm in a city that isn't exactly transgender haven, but I feel like I have a lot more leeway for learning and making mistakes and familiarizing myself with the system while I'm still in college.
Look at all this progress I'm making all of a sudden! I'm finding more resources than I even thought existed here in my city.