I'll answer the military branch first because it's easier.
Cadets from West Point commission into the the Army. In my case, it would've been the Air Defense Artillery branch of the Army. It's like the Naval academy and Air Force academy. West Point is called the military academy simply because it came first. Although some cadets do cross-commission into other branches. I have a friend that became a Marine officer, and there's usually one every other year that joins the Navy in hopes of becoming a SEAL.
Advice for someone questioning, I'm going to word it in the second person: simply put, nobody can make that decision to transition or not, except you. It's entirely personal and entirely up to you. It's not an easy path either, far from it, but it has its rewards. It comforted me to know that there are transgender individuals that don't transition either, and that I have options to live my life how I want to live it. If you like wearing dresses, regardless of your gender, wear dresses. If you want to wear a suit and tie, wear it. It doesn't have to conform to your identity and visa versa. You may not really mind the pronouns you currently use, but you might using the other pronouns a whole lot more, who knows?
It wasn't until I met another transgender woman (my own age) and saw how alike we were and that I fully identified with being trans. The advice she gave me was that at some point you just learn to not give a fuck what other people think about you. Even being trans I dress boyishly (exhibit A: my pic) because that's what I'm comfortable wearing. I just so happen to prefer female pronouns as well. That advice seemed silly to me in the beginning but it's made a lot more sense as I've gone out in public more. Hopefully that helps.