I always thought I was just an introvert and shy, but as I’ve been transitioning (still early) I’ve felt more confidence than I thought possible. I don’t expect to turn into an extrovert, but it’s an amazing improvement so far! You say you’d transition in a heartbeat if society was more accepting, but if that’s the case I recommend doing it anyway, or at maybe just dipping your toes in. Maybe you can try being a woman in private and a man in public, that way you don’t really risk anything while still being able to experiment.