The first set of Dave’s trans jokes included him basically saying that while he doesn’t understand trans people, he ultimately accepts them for who they are. In that era I defended the jokes because I felt it was valid to joke about stuff as long as you ultimately aren’t trying to hurt, belittle, or delegitimize ordinary people. The follow-up jokes weren’t nearly as understanding and I no longer felt like Dave cared about much beyond being a dick. He seemed to double down on the punching down without bothering to build them back up again.
Anyway, there is a fundamental difference with Trump, in that he’s downright a fascist, so joking about his death isn’t exactly punching down. It’s more like wishful thinking.