I was on a forum where the creator mentioned that if Sigmund Freud was alive today he would be a fan webcomics. Since "Someone like him would probably find it fascinating how these supposed works of entertainment so often contain thinly disguised confessions of deviance and clues to a wide range of abnormalities in the authors' psyches."
There's some that would interest him the most…
Pibgorn and 9 Chickweed Lane: A possible reverse Electra complex, impalement fetish, women who are either old biddies, sex crazed, bitchy, childish or a mix of it; a number of men look like the creator.
Least I Could Do: The self-worshiping misadventures of an obvious self-insert who is free to treat others like crap and go through women they're disposable. The fact that he gets away with it and is often rewarded for his selfishness might interest him even more.
US Angel Corps: That is he if he can make it past the first story.
Anything By Jay Naylor: Twincest, hinted Odepus Complex, issues towards women and minorities.
Anything by Bleedman: (Especally Grimm Adventures)