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You might want to consider giving some guidelines and rules. Things like "Must spend each day looking for a job" and "You can only live here X amount of months". It may sound a little harsh, but it doesn't sound like you are set up in such a way that you can help this guy for an unlimited amount of time.
Giving a helping hand is nice, but don't let him become to attached to it.
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This too shall pass.
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