Thanks for the comments! My brother used to play at nursing homes actually, but there's no telling if he enjoyed playing for such audiences. He slowly stopped doing that, I guess because it requires regular contact with the nursing home administrators, since the gigs weren't regular. I know he loves to play piano and perform, so it'd be great if he could do that again.
I don't know if he'd be miserable in an office. Maybe it would be too interactive for him, but I can't see a lot of other jobs in sight, and really hope he doesn't get stuck at CVS or stop and shop for his entire life... At least in an office he could fix computers and have hopes of promotion, and maybe increase his social skills.
I did think that an enforced schedule could help, but as he gets older, the ability of anyone to enforce anything in him is less and less. My dad can't even get him to do chores around the house. The only thing that got him motivated was when his computer was taken away until he could get a job (he was unemployed for around 2 years and living at home after college). That may be the only thing that will get him going this time... though all it did last time was get him a job at Stop n Shop