Exactly. Chris is too invested and has gotten too old to ever renounce these beliefs simply because he would have to cope with two decades of his life being absolute garbage and wasted. It's very telling with how much he adores his high school days, whereas they were pretty boring or average the way he describes them, but that was the final time where he had zero consequences or real life to deal with. I think you're spot on with Chris getting scared of the future more and more, which is why I think Flutter really is gone, given the way he's acting lately. If she was his actual girlfriend, and was genuine, losing her could throw his "future" into serious jeopardy since he probably assumed she'd always be in it. Now he's back to being regular old, naive, tard rage, lonely Chris Chan.
I still think he went to HarmonyCon because he needed social interaction because she's not around anymore, and when he was thrown out, that caused him even more emotional damage because he figured the brony cons were one place, pre-Barb breaking, where they "accepted" him, even though that meant no one interacting with him. I seriously hope we see some more unban contracts or Chris groveling at the reg desk of some other convention he desperately wants to attend.