As other people have pointed out, with his tugboat, maybe augmented by the occasional eBay sale (if Chris gets smarter about running his "business") Chris could scrape together enough to be able to afford a studio or 1-bedroom apartment, especially if he looks in the smaller towns surrounding Charlottesville, where the rent is likely to be a lot lower.
If Chris were a little better with his personal hygiene, and less obnoxious over all, he could probably find a roommate or two and get a nice larger apartment, maybe even a small house.
Getting away from Barb would improve his life immeasurably. From what we've seen, Barb can take care of herself without Chris, and she'll be just fine if he leaves. If he ever wants to salvage what's left of his life, he should leave as soon as he can. This should be his priority. Barb is toxic and she's ruining any chance Chris has of living a normal life.
If, by some miracle Chris managed get his finances sufficiently in order to pull this off, then a lot of us here would be cheering him on and wishing him well, myself included.