I don't really see that happening. Chris is generally pretty cowardly in person.
Chris is intellectually and physically capable of doing a lot of entry level jobs. If he ever gets it into his head that having a job something he needs to have, he can probably get one. It doesn't seem to be that close to happening, although I would say that with his online business he has realized that a) sometimes the tugboat doesn't give him as much money as he would like and b) there is something he could do about it. It seems conceivable that line of thinking could evolve within the next few years towards a concerted effort to get a job. I am not putting money on it, but I wouldn't rule it out. He does seem to feel entitled to lots of money without working, but he isn't going to get any more than the tugboat, so that feeling can't stand. The internet business is proof that his sense of entitlement can be broken.
Would he fuck up? Probably, but probably not as badly as people here portray it. The most likely issues are shirking and bothering the customers. I think he needs black and white rules. If you say to him "be friendly to the customers, but don't bring up trolls/Sonichu/lesbians" he probably can't handle that. But if you say "The only things you should ever say to a customer are polite answers to direct questions", he might be able to. In the end, I think he would iterate towards being able to function at low-end jobs. He might learn a few lessons, he might get fired a couple times, his supervisors might have to figure out a few tricks of Chris-wrangling, but I think it would be ok in the end.