Clearly we disagree about how to evaluate comedy, which is perfectly fine, but I think we’re running into a wall at this point. I think most of what you’re saying is reasonable, we just have different perspectives. I think this quote highlights that best:

It’s not his lived experience, so what could he possibly have to add as an insightful observation?

I don’t think you need to experience something firsthand to make jokes about it. I also don’t think comedy needs to involve insightful observations. That might be the kind of thing you find to be the most funny but that doesn’t make it a rule that needs to be followed at all times. Something you find unfunny, or even offensive, can be a genuine attempt at making people laugh. The fact that you find it offensive doesn’t necessarily mean they’ve done something wrong. In many cases it just means that you don’t like that style of comedy. A comedian telling a joke during a comedy show is not the same as a politician or other public figure justifying a bigoted statement by calling it a joke. Choosing to interpret comments that are clearly and obviously presented as jokes as some sort of expression of a deeply held belief does not seem like a logical approach to me.