I'm still catching up on this thread, but I've read about Dobson on the EDForums and on SomethingAwful.

This sentiment has come up briefly in this thread before, but I agree in thinking that Dobson is literally addicted to getting attention, whether good or bad. And I also believe that he does everything in his power to get that attention, and that he's really not "clueless" so much as that he's hellbent looking for any and all means to bring that publicity upon himself.
He always whinges and complains about how "DeviantART ruined me!!11" and how he doesn't like to draw anymore because the "haters" took away all of his motivation and willpower... yet any person with two brain-cells to rub together would've left DA a long time ago or at least have made a new account and started over if everything was really "that bad" (Snapesnogger is one lolcow who comes to mind that did this, and she is pretty much a non-issue nowadays). Likewise, he spastically writes on Twitter at all hours of the day making inflammatory remarks, and despite any help that comes his way, he continues to make an ass of himself. When he says things like, "
Other M is the best
Metroid game" or "
Ocarina of Time sucks", I really can't help but believe he is just saying these things to give himself an audience, and that he probably doesn't even hate those games as much as he says (or even hates them at all!). Same with the Nintendo fanboyism and hating everything PS/Xbox (even the
Arkham series), everything is done to give people something to yell at him about.
Honestly, would anyone even be following Dobson if it wasn't for his unabashed horrible attitude? I know I wouldn't... Take away the whinging, the "troll-bating", the Fad of the Month cause that he's rooting for at the moment, and what would you have? A mediocre artist who draws bland, mediocre comics.
His other comics, Alex ze Pirate and Formera (sp?) don't get NEARLY as much attention as SYAC does. I think, because other than a few much more minor problems, they're so terribly boring and amateur, there's nothing really to write home about. Please correct me if I'm wrong, but didn't his SYAC comics go pretty much unnoticed until he started using them as a soapbox to whinge and complain about some perceived unjustices in his life? I think that when he started seeing that people were reacting negatively to it (but reacting, nonetheless), he took that idea and went with it. Now every single one of his comics is smug-ass pandering to get attention. AFAIK, he doesn't even write AzP or Formera anymore. So much for wanting to be a cartoonist and getting his work out there.
If Dobson was as serious as he says he was about drawing, he would've changed himself and/or his work a long time ago. As it stands, I think he KNOWS that his comics are nothing but bland tripe and that he has NO hope of getting into a professional "biz" as he calls it, so he uses DA to fill that hole left by crushed dreams. He blames his failures on his haters, but he never had any success before they even showed up. Being a horrible person was the one thing that finally brought attention to himself, so now he's running wild. I think Dobson can't even stop being such a jerkoff at this point because to do so would lose everything. Some people mask their depression with drugs or alcohol; Dobson hides his by drowning himself in attention. When I read his past journal entries about how he hates anime because the club members didn't want to watch what ~* I *~ wanted to watch and whatnot, it sounds like he was always an attention whore, but never grew out of being a huge manchild. Now it's in full blossom. Being a cartoonist was just a means to get that attention (which in itself isn't bad; people have lofty dreams), but now since it'll never happen, might as well make waves being a full-on idiot.
Sorry for my armchair psychology long post. tl;dr: I think Dobson is purposefully doing all of this for attention and knows that he is.