I think the "problem" with Chappelle's recent standup specials is that people are misinterpreting his jokes, and his specials contain subjects that are easily misinterpreted to cause harm. But that's not really his fault that's the audience.
In this special he tried to "get his story straight" (and it's one of the better "comedian defending himself" style stand ups even though it's an awful trend that needs to fucking die already) and I think he does a decent job. I think yanking one line out of his special and painting him as transphobic or a TERF does more harm than good tbh. I know TERFs and transphobes (irl and they're all fucking atrocious people) of all kinds and they wouldn't speak about the trans community in any kind way at all. They don't even view trans people as people at all. Watering down these terms to include someone like Chappelle is bad imo. Now we have the TERFs and transphobes defending him only because people are calling him out for being transphobic when he clearly isn't. This whole discourse has transcended the content of the special at this point.
At the end of the day he's comparing the trans experience (or moreso the LGBTQ experience) to the black American experience but it all basically boils down to white people. And he makes decent points.
Saying the LGBTQ community is punching down on the black community is pretty fucked up and now we have a bunch of right-wing shitheads suddenly supporting a black man playing "oppression olympics". Not because they give a fuck about Dave or the black community's struggles, but because they hate LGBT people even more.