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There are other resources out there to help him. I went to Vocational Rehabilitation through Social Services for help in deciding where I wanted to go with my life since I could no longer work jobs on my feet all day. They purchased a new computer for me (my very old computer was hit by lightning last summer), and I'm enrolled full-time in college for an associate's degree, all online. They also pay for any college expenses my Pell grants don't cover.
All states have HUD programs as far as I know that will pay most if not all of your rent if you qualify (low income). Social Services should be able to provide that information to him.
I can tell you his self-esteem issues are not going to resolve with you handing money out to him.
My parents currently help me financially while I'm in college, and although I appreciate it with all my heart, it also makes me feel bad, and I can't wait to graduate and get into the field I am studying for so I can be self-sufficient again.
It's hard to take the emotions out of it when you are dealing with your own adult child, but that's where I got myself into all kinds of trouble with my AD when I was coming from an emotional standpoint.
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DeVon & the Zoo Crew  Worry is a thin stream of fear trickling through the mind. If encouraged, it cuts a channel into which all other thoughts are drained. ~Arthur Somers Roche
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