You are in the right place, Taylor.
There is an awful lot packed into your message.
It’s difficult to answer all of the questions as there is a cascading effect – at least there is in my experience.
He needs to truly understand himself first, and fully – as you suggest.
It’s probably best done with a counselor.
Any conjecture here on the ‘why’ any of us do what we do could bring unnecessary false imaginings so I won’t.
Based on what you wrote, I’d think your mind is in a bit of a swirl so all I will suggest is the simple ‘one day at a time’ mantra. Breathe.
There are a lot of articles for the SOs on this site. I would encourage you to check them out.
I will say we are all a bit different as to how we acquired our imprint to be feminine. How far any of us goes on our journey depends on a great many things. It’s not as simple as slipping on a pair of shoes.
Please read and keep asking questions. It’s how we all learn.