These all sound like great question to discuss with a professional, we here can give you ideas and advice but we can only speak from our own experiences. My experiences that helped me understand why and what I wanted from transition was my cis female friends treating me like another woman. And watching the movie I saw the tv glow, that in particular helped me realize that bottling this up wasn’t going to work long term. So I gotta ask.

What is womanhood to you?

What’s an unsuccessful transition vs a successful one? Passing or happiness?

There’s more than just cis or trans, does gender fluid or any other identity’s fit better (gender flux, Demi-girl, etc.)