Fye just because he doesnt have everything at his feet doesnt make him a loser. Jobs are extremely hard to get, at least in my area, and you cant expect him to get an apartment if he has no money!
Sounds like to me he's doing all he can. Like I said if he has no money he cant get a lisence or a cell phone (why is a cell phone important?) or any other materialistic thing you might want him to have.
He doesnt want help because he doesnt want people to give him everything, he wants to earn it himself..I'm the same way.
I think honestly this is more about you. He's doing nothing wrong...these things do take time. Be patient.

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