It has nothing to do with the sex change, or how not particularly attractive a woman she is.
Which brings me to my disclaimer. I know two people from the filk world who went through the complete sex change. Both from female to male. One was a DDG woman whom I admired from afar, who is now a DDG man. It has vastly changed his music, in some ways for the better. In most ways just different. The other is a friend, whom I only knew slightly as a woman. She had a girlfriend who was also a gifted musician, and not long after her girlfriend passed away, J started slowly changing. And I got to know him better over the years and count him as a friend now. He hasn't performed much music since the change, but he's still very active in the filk community. As far as looks go, I'd say he was an average looking woman who became an average looking man. Though he's in better shape than she was.
The only person I know who was born a man and claims to identify as a woman is not someone I know well at all, but met a few times at some concerts, and it was clear that she's too proud of her very large penis and the women it attracts to make the change. In my book that's just a costume change.