with ssi he would at least have his own insurance. Its an aggravating process but i dont think its humiliating.

I dont know enough about what your sons particular disabilities are but maybe a hands on type of occupation would be good for him. Less book more do kind of thing. I know kids who had low self confidence who then by learning a skill felt much better about themselves.
Welding is one thing that comes to mind and you can do a lot of creative work on the side with that skill.