Chris has some decent male peers in his life. Even "Santa Claus". This didn't do any good for him, in fact he decided to make a special list of "men I don't hate" just for those peers, instead of just realizing that maybe, just maybe, males aren't inherently malicious.
Chris' issue is that he's all Id and no Ego. When you get down to the brass tacks of Chris' psychology, Chris is straight. He wants to fuck women. And his stupid idiot brain just doesn't understand how he's supposed to handle those urges while also communicating with entities he doesn't want to fuck. He doesn't really see the value in acknowledging an entity he doesn't want to have sex with, or otherwise won't give him something he wants (although getting things he wants is far less important than getting to bone something). His auto-gynophiliac tendencies kind of show that. He can't really understand things without first placing them into a situation where he gets to have sex. Or, more specifically, situations that appeal to his sexuality, getting to see naked women. Like any asspie who likes lesbians/yuri (e.g. Dobson), he's a broken idiot who don't understand the psychology and technicalities behind mating, he just wants to see vags, the more the better. There's just something missing, some inherent primitive failsafe for mammals from wanting this dumb shit so they don't inevitable devolve into wanting to see entities of the opposite sex mate for their own amusement. Again, it's probably something Ego-themed to prevent the Id from self-destructing like this.
I think Chris' current path was inevitable, there's not really much I could imagine would change it. With proper counseling and not being enabled by the insanity of twitter, sure, maybe he would have not turned into a bag lady who thinks Bugs Bunny is real. But otherwise, I think someone would have enabled his broken putty brain into these delusions, something deep seated within his psychology, and ultimately it would have surfaced anyway. Even if he understood how to hold down a job or otherwise manage his own finances, he would have inevitably trooned out, become an outcast and isolated from the world due to a persecution complex from the criticisms he would have received, and ultimately would have fell into his imaginary world anyway. We've seen this from other cows before, they had decent lives and jobs before trooning out, and then became literal Gollum imitators.
I don't think Chris ever had a chance. Maybe it was due to his genes alone, he was born from fucking senior citizens after all. No matter what the cause, Chris never seemed right to me, and his behavior really suggests that it stems from something extremely primitive and deep-seeded in his mind, not something he picked up later in life, definitely not something developed past his pre-teenaged years.