College

Okay so I can't answer all your concerns but I can address a couple I think.

Telling everyone: you should come out as much as you are comfortable. Maybe do a search, see if any alumni were out as trans to the school and what the reaction was. If there's an LGBT+ group, get in contact with them maybe?
This goes for your name too, tell the profs and peers and paperwork your name if/when you're comfortable (depending on the size of the school, your profs might not even bother to learn your name).
About dorms, is there a co-ed dorm? Depending on the school's rules and regulations you may be forced to room with your assigned sex. I know sometimes there's a 'special requests' kinda thing so maybe you could request to room with someone LGBT+ friendly?

You've got so much time to think about this! See if you can't find an anonymous way of asking these questions to the school, like a message board or email or something.

 

I think if you're ready than college is the best place to be out, depending where you go. I'm excited to go back to college specifically for that reason. That's generally where you'll find the most open minded people, and the most opportunities to meet people like you.

 

I would plan to be out. College gives you a fresh start. For the names, the best thing that you can do is email your professors with a small explanation of what your legal name is, and what you would like to be called. This is the email that I sent to my professors before I had my legal name change.

This way, my birth name was rarely mentioned in class. There are some things that you will still have to use your legal name for, but the professor can talk to you about what those things are.

For dorms, I would get in contact with the residence services at your school. They usually have accommodations that transgender people can use. It also will be worth looking at their website, because often times online they will have an explanation of their transgender housing options and how to opt into them.

Sometimes if you google your school with the word transgender, you can find good info that way too. This way, sometimes you can find experiences that transgender students have at the school that you are looking at.

And finally. you said that you do not want to start T until after your first 4 years. I would look into seeing if there are any therpists that have experience with transgender people at your school. I got lucky with my school having one. Colleges have discounted rates for therapy, so it's something to take advantage of if money is a concern. They also can often send you to trans* accepting endo's (which is something that is very important).

I would also look for student groups for LGBT people or transgender people. They can help you find resources on your campus as well.

 

Hey Tai! I actually just finished applying for college a few months ago, so hopefully I can offer a tiny bit of advice.

Unfortunately, you'll have to use your legal name on your application. After you get accepted, however, you can email your professors about using your preferred name so that students most likely won't hear your birth name read out loud. As to coming out, just do whatever it is that makes you feel right. Non-religion affiliated schools are usually pretty supportive if you come out to them, and almost every university has a LGBT group you can ask for help from. Some even have LGBT specific counselors you can talk to. Christian-affiliated colleges tend to be more hostile towards trans* students though, so that would be something to consider when applying to schools.

I'm personally going to try and go stealth when I'm in college. The great thing about university is that you're legally an adult, so you can tell the people you meet whatever name you damn well please. You have no obligation whatsoever to tell anyone your birth name (well, aside from police and authorities but you know what I mean :\).

Still, there are probably situations where it's best to come out. Dormitories are a pretty big example. I know that certain more liberal colleges have gender neutral housing for trans* and non-binary students (unfortunately the school I'm hoping to get in doesn't, but ah well). I actually share your discomfort about roommates, since I wouldn't be comfortable rooming with a girl, but having a guy as a roommate would also make me feel...inadequate, I guess. I think it's possible to try and request a single room so you don't have to share with anyone, though I feel like that's not exactly fair to cis students who have to room with another person.

 

Two thoughts: try making contact even before you get there with the campus LGBT center. And look on the school's web site to see if they have policies or guidance for trans students.

A few months back, I did a quick search on my alma mater's site, and was pleasantly surprised to find that they had several pages, detailing how to communicate your preferred name and pronouns to your professors, what to do if one of them Mis-names or misgenders you, and a bunch of other good stuff.