I'm in the school of "Chris could have had a menial job but..."
What he would have done would have been a constant problem, i.e. needing supervision, special consideration of where he's placed i.e. his Wendys job was in a public facing capacity can you imagine if he brought his love quest into work or was there long enough to develop feelings for someone etc? He would refuse to do any physical labour, hell he would also refuse to stand for a prolonged period of time, he'd find ways to goof off or become a active neaucance to other staff etc.
The sort of job he could do he'd not like to do as it's either outside his comfort zone or required him to develop some form of physical fitness etc, the best thing that could have happened to him was getting the tugboat as it kept him fed, in some level of comfort and most importantly out the way (ok with varying success) of people who wanted to work in jobs for special needs people.
I can imagine Chris working in the Salvation Army or Goodwill. Those places are optimal at hiring a huge amount of tards. Also, Chris can get himself and Barb (before the romp in the hay), a discount. But, as it's often noted, Chris always has to push back against management and has problems with supervision/people with authority over him. Not just at Wendy's but places like PVCC (his English professor and MLW), as well as the manajerks. I keep scratching my head as to why Borb never saw Chris as the problem and blamed everyone else but him for his actions. Sure, autism, but even they (or at least Bob) should have looked at Chris' fuck ups and did something. I know Bob tried with the mainstreaming throughout Chris' college years, but fuck, did that fail. Chris' sense of entitlement is telling with his 'negotiation' videos. Even though he says to SEGA and Nintendo, he wants a top spot for licensing sonichu, he's never worked for it; it is always what he imagines in his cartoon scenario.
The more I think about it, the more I'm MATI at Chris. Most of it is his laziness, but to top it off, his entitlement and narcissism and his choice to hold himself back from getting a job, even though it would be to pass the time and earn some extra money, he doesn't want to because people already know of him (which is true because he fucked up for himself), and he's never learned any skills. I don't know about CutCo, but if Chris was asked by the manager of the glass sorting place why he left Wendy's, he'll probably answer with "management was cruel to me" or "look it up on the internet." Any other special needs person would be jumping for joy at the opportunity a job would be given to them, but not Chris. Because he thinks he's better than them. I will say Chris struck gold because of his 'artist' (lolcow) status, but Chris has proven once again that he fucks himself over by spending way beyond his means, and tard rages for not mailing his junk in a timely manner to people who are more than willing to buy his shit.
As usual, after release, Chris would get lucky and unironically have people buy from him, but the cycle would end up repeating itself until Chris really does end up homeless, post group home, if it come to that.