JessieW123 on youtube. He's a ftm and is going through his transition. I contacted him and he was wonderful about giving me advice. My partner and I will be there next year, and we are both super amped to go back. We both did study abroad trips in our younger years.
I feel you with the language though. I have been studying for years, and I am a TA in a Japanese language class, but whenever I talk to any of my Japanese friends, my language skills go flying out of the window and I resort to miming and making an ass out myself in general.
Luckily though, the Japanese are pretty good about just letting the 'henna gaijin' do their thing without too much hassle. If you are planning to live, work and go to school there (between me and my partner we are doing both; yay for employment and grad school!) then there may come a time when you have to conform a little more to social norms. But from my understanding, just being a foreigner will allow you a lot of wiggle room. Also, from Jessie's experience, I gather that transfolks have an easier time than cisgender homosexuals. Funny double standard, ne?