I think a good general principle is “don’t punch down.”
Transgender people are in a tiny minority and are the subject of much scorn and political oppression right now. They’re scrambling for the right just to BE, and to be in relative peace.
Chapelle’s jokes felt terrible to me because I felt he was punching down.
In fact, I vowed to never watch another of his shows. I’m done with him forever, because he doesn’t seem to understand decency and sensitivity. As a member of an oppressed minority, himself, he really ought to have known better.