I might try to put one together.
Chris is very consciously worried about how screwed he is when Barb dies. He's talked about it on facebook.
But if you're wondering if he's aware of all his fuckups? Probably not.
Like, consider his face blindness. It's not that Chris can't see faces at all. Chris can see the various details of a face: nose, eyes, mouth, ears. But when it comes time to look at the overall picture, and see how they fit together to make a coherent whole, that's where he falls down. When someone's eyes are too close together, or their face is a bit too long, those features are too subtle for Chris to recognize consistently.
Chris' view of his life is like that. Chris is aware that getting arrested for stuff is bad, and he's aware that it's not good to be unemployed for too long. But he hears about other people getting arrested (for little things, like say a college prank) and other people being out of the workforce for awhile (maybe they got sick or had to care for children or family members), and Chris wonders what makes those people different from him. All the differences he sees are superficial.
Any comparison involving scale or scope is probably going to be too subtle for Chris to master. Especially if Chris is one of the things being compared.
A minor theory I've got is that that's why, when talking about sex, Chris focuses on breasts and vaginas, but he completely ignores things like overall body shape and features like butts. The difference between a nice ass and a flat, uninteresting ass, is too subtle for Chris to scope out. Primary sex characteristics are very important to Chris because they're difficult to misidentify.