I think Dave is just in a weird position. I think he genuinely wants to be liked and seen as "everybody's friend," but he also sees himself as a comedian's comedian and to some extent you can't be both. These past few specials have been his desperate attempts to convince his critics that he's not against them while also making the kinds of jokes that he thinks will be respected by his fellow comedians. Shit doesn't work.
My bigger problem with the special is basically something
@Race Jones alluded too. Too often now he says shit that just isn't witty or funny. It's like he goes on some commentary rant and then remembers he has to try and make it a joke and the shit falls flat. A good example of it was the whole MeToo rant. Like he was making reasonable points and then he capped of with the "You should make me a leader. I'll get you everything you want if...you suck my dick." I audibly groaned at that shit. I was expecting him to come with something better than that.