His Jim Carrey story just made me feel sad because it made me believe that he really doesn't understand. Jim Carrey was trying to become someone he truly wasn't. Someone, whom is trans, is trying to become the person they truly believe they are.
It made you sad because it's anti-trans.
Chapelle, in that cute little anecdote, is literally denying the existence of trans identity and claiming they're just acting and it's a choice. That is the way that the right is trying to erase trans identity, and it's the same playbook they used when attacking the gay community (i.e by claiming it's a lifestyle choice and not an issue of identity).
As for him not "understanding", bluntly, that is a choice. He's not some misguided poor soul. He has access to all the information you and I do. He could educate himself. But he's made a decision, and that decision is to deny the existence of trans people.
Frankly, it seems to me your fondness for Chapelle is leading you to downplay his beliefs and his behaviour.
Tetris Effect finally got me...