Never liked Daquan. Whether the images are being created by white people or not, the joke just isn't funny. Plays into white American hysteria over hyper-masculine black men ruining white women.
I haven't watched much of Chappelle, but I'm more comfortable with this kind of humor in the two seasons of The Boondocks I've watched since it's all centered around a black family. By virtue of having more black characters on screen they're able to have blacks who aren't complete caricatures in addition to the more stereotypical ones. You don't actually see Daquan in most of the images. When you do, he's exhibiting some type of stereotypical behavior. In The Boondocks you at least have Huey Freeman as your straight man. In some of Chappelle's skits he also just a dude reacting to all the weird shit happening around him (though I'm sure there are plenty where this isn't the case).
Daquan meme is just the latest example of media where black people only exist in the context of how they impact white people. Both The Boondocks and Chappelle's Show have some instances where black people get to just "be," which is something I really appreciate.