Wow Lufia, those are some tough questions. Your situation seems complex.
I’d love to offer advice, but these are the kinds of things that can have serious consequences in life. These are not the kinds of decisions one makes based on message board feedback. Have you spoken to a counselor or therapist about all this? If not, that’s a good place to start.
Coming out to ones family can be really good or really bad, as we all know. Some of us have lost our family ties as a result. Are you prepared for what could happen?
I’m definitely not qualified to advise anyone on anything, but if a path forward is what you seek, I’d say it likely begins with independence, or at least the ability to be so. You said you were working on that, and maybe thats where the solutions you seek are as well. That’s probably the best way to make things easier on everyone, including yourself.
Coming out is its own challenge, but you asked about transition. I personally feel that should pretty much always start with a therapist. The next steps after that could be medical, like HRT, but those next steps are best figured out after talking to a professional that can answer your questions, offer recommendations and referrals, and hopefully get you on the right path to happiness.
Good luck, whatever you do.
Edit to add: Many of us never come out to our families, and that’s okay. There are a zillion ways to do this thing we do, and not all of them require transition. Many people transition and still don’t tell their families. There are degrees of Coming Out, it doesn’t have to be All or Nothing.