I wouldn't be afraid to kick him out on his butt. A college student recently took a year off to essentially become homeless on his own free will. He left behind his education, family, credit cards, home, everything. His goal was to have a steady job, a place to live, a car, and some savings after a year. He had achieved all this in under ~9 months (I believe), without even utilizing his education, but had to end the experiment early due to a family crisis back at home.
The goal was to simply learn from the experience, and write about it at the end. He was confident that anyone could achieve the same things he did. Google it, maybe it'll give you (and him) some more confidence.
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