I kinda felt the same way while watching the special...very much the 'is he really trying to say he has a trans friend'.my issue with Chappelle is that the trans community accuses him of the same thing he accuses white people of. He literally had a "I had a trans friend so I can't be transphobic" bit. He talks about empathy being a two way street but then refuses to look at how else that street can be applied.
It was somewhat cringe, right up until he said that she was 'his' tribe not 'theirs'. I thought that was incredibly poignant, and for me sort of flipped that narrative. He wasn't saying 'look at me, I have a trans friend so I'm not transphobic'. I think he was saying 'i accepted this person as part of my tribe, but her other tribe rejected her in her last days'. As others have said, I think it was much more of a statement against the toxicity of the community than a baptism by friendship.