Hey November Fox
I personally had on and off fears about transitioning myself. Now looking back, I am glad I did.
I sort of come from the same headspace, and by that I mean I thought I would just be a unhappy "girl" the rest of my life basically because I didn't think I had any other choice. Before I understood the T word, (trans), I knew I loved everything from skateboarding to wearing men's clothes, but I didn't think anything of it. That word "tomboy" really had me locked in.
When I started transitioning though, I began to be a much different person. My parents noticed I was much happier, much more confident. I started with the name change, because that was the first thing that had to go. Then I did HRT. Here is the part where I was nervous, scared on and off....I honestly didn't know what I'd look like or feel like on Testosterone... And I felt some of the changes may not have been for me. I don't remember what it was that helped me get through it, but I'm pretty sure I was going to turn around on the day of my first shot and go home.. but my grandma had ridden the train all the way to my part of town to learn how to do it for me and I felt I couldn't waste her time. I'm weird like that. Once I started getting the hair, the side burns, the vocal changes.... I knew it was for me and I never looked back.
I had top surgery 3 years later and though I have my regrets in terms of the way things look (I probably just would like a revision), I do not regret the surgery itself or my decision to do it.
If you ever want to talk, you know where to reach me

I hope I answered some of your questions, sorry I rambled a bit.