I think he has a few people that enjoy his streams in a parasocial fashion. Like they enjoy "hanging out" with Wings or something like that. There's no way anyone is actually there for the gameplay that's true. But streaming is often more about parasocial shit than having killer gameplay anyways (just look at the popularity of twitch thots).
He has trolls because he always reacts and lets them get under his skin, he can't help it. That's the basic reason that anyone has trolls, because the trolls are able to get reactions. I think it was literally last night or maybe night before he was doing one of his "just chatting" streams and he just complained about too many trolls in his chat asking him about Shailene/Brandi and shit like that then ended the stream.
I do think his trolling gets turbo-charged by the fact that he embodies an extremely hateable stereotype, maybe the most hateable in Current Year, namely that of a fat dumb egotistical redneck. Even though that's not fully who Wingo is his appearance and manner conveys it and I do think that makes it easy for people to dehumanize him.
And I will also say that I just plain don't know how to explain the levels of turbo autism that we can find in his "trolling community." Like to the point of having literal "troll civil wars." Not sure that I've ever heard of that with any other lolcow lol. I don't think I've ever even seen the term "troll community" anywhere else, maybe with DSP who has his "detractor community."
I imagine he is trying to raise clout among his fellow "Wings trolls." Hence the motivation to put out videos shitting on Wings by any angle possible regardless of whether there is anything funny actually happening.
Nah he's not autistic just dumb lazy and no impulse control. Not everything is autism, plenty of people have those traits for no real reason other than they just do. His "depression" is easily explained by the fact he's been a land whale his entire life and hates himself for it. Depression is more of a true mental illness when it's experienced by people who have nothing to really be depressed about. But if you have a shitty life and/or you're a piece of shit, then you're probably not depressed because you are mentally ill, you're depressed because your life sucks. I think this is part of where Richard's huge fragile ego and need to be the best at CoD came from before the trolls broke him, it was him compensating for his bad self-esteem due to his physical condition and low social status.