In most of these instances, Chris has had his worldview stepped on and underscored as being completely wrong, but every time he always retreats and doubles down on himself being the super special person the whole world should be spoiling.
The driving motivation is simply avoiding difficulty of any nature that does not present immediate short-term rewards, then as he's gotten older he pines for the nostalgia of his youth when life wasn't so harsh and complicated. CWCVille, then eventually whatever Rick and Morty bullshit it got warped into, was the world that accepted him unconditionally without him having to make any effort whatsoever at getting along with other people. After all, he was perfect, why should he change? It was, and really on some level still is, the world that should change for him as he believes it.
That's why it's so easy to manipulate him if you play into his fantasies. He NEEDS the confirmation he's the special one, which is all he got as a child but as an adult nobody has time for that shit except I guess Caden. It's all a childish game where he refuses to grow up, nothing more.