First thing I'd look into with your school, is what sort of non-discrimination policy do they have? If it includes GLBT folks, you are probably OK. Legalities are going to be one of the toughest parts about transitioning. What does your state require for state ID's to change for instance. Documentation is one of the hardest parts to handle, so be prepared for a headache or two.
Transition happens at its own pace, so don't stress about that. I was lucky in that I had a therapist who wasn't invested in any outcome for me. She was open to the idea I was trans, but didn't make her living from people in transition. I'm a little conflicted as far as timeline for my process. On one hand, I wish I had started earlier - on the other, taking more time could have helped me ease into my life. In all though, I feel like people transition as they are able to and at the right pace. There is no expiration date on it, and it can be emotionally and physically taxing - so take your time and enjoy the process.
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