I have finally gotten around to watching the most recent one. Chappelle is funny and also a really good storyteller.
The use of "phobic" is a little strong and misplaced to me. I truly fear snakes for instance. They can harm me. I do not think Chappelle thinks he is going to be harmed by a trans person at least not because they are trans.
Chappelle makes some jokes about not wanting the hugs of a trans person, but they are just that and only the most insecure can see harm in that.
The story about Daphne is funny and then heartbreaking. Chappelle's words (as best I can tell) have never killed a trans person, but the people in that community may have played into the suicide of one of their own.
I also watched his previous show. He does spend a lot of time on the LGBTQ thing. Some of it is very good stuff like the comparisons of how long it took LGBTQ to get freedoms that were denied black people for a lot longer. (I would argue the civil rights movement and the big swing in that paved the way for gay/trans rights.)