Does Chris have the ability to look at his peers that are now his age and compare his situation with theirs? Even if he did, he'd probably use the fact that he's got trolls as an excuse as to why he wasn't nearly as functional as they are.
He's gonna blame any perceived shortcomings on his trolls, the greene county conspiracy, discrimination against autistics/translesbiansoulclit-people or whatever else he can come up with.
And that is if he perceives any shortcomings at all.
Assume someone he knew during highschool was married to his girlfriend from back then, Chris would happily announce that he had more experience with girlfriends since he had half a dozen real/artificial ones or something.
In the same manner, a womanizer would be scolded for being a vain brute that doesn't appreciate (and thus deserve) a girls love.
If they have something unique, Chris tries to overshadow it with something of his own accord.
If they have less than him, he mocks them for it.
If they have more than him, he's gonna mock them for imaginary reasons he's gonna pull out of his ass cause whatever they own (that he doesn't) is attributed together with something bad in his cartoons. (ie: rich people being assholes)
And if everything else fails, he clings to the royal Weston heritage.
It's a bit like with Cole, who was supposed to be rich and well educated, where Chris basically twisted it so the 'rich' meant Cole was bigoted and shallow while he tried to trump Cole's doctorade with his Honor Roll.
Deep down, in some moments of self-awareness, he might understand that he's worse off than anyone who went out to make a life of their own, but unless something really dramatic happens, he's not gonna admit that.