I like you described example ... But just as you, im probably also blind to some aspects that may be problematic. :-/
So far the only character i know in games, that was trans and it had significance for story, was Krem from Dragon Age: Inquisition: - Born as a female > wanted to be a Warrior, and was good at it > joined Qun (not sure if before or after) > in Qun only males can be warriors > so by their definition Krem was a male And was happy that way.
I still dont understand why cant we change Race for our hirelings. Lets us play Githyanki as racist as they trully are!