I See Two Issues

Chi, I see two issues.

1) You want to help the guy.

2) You could use the money.

It was suggested to you in a way that conflated the two issues. Now, separate them instead.

If you can help the guy in any other way, do what you can. But renting to him? Too risky.

If you see a way to make money renting, take the good advice above about finding good tenants.

Oh, the experiences I could relate, both in "helping" friends who nearly ruined me, and in 14 years of being an evil landlord in Chicago. My advice, nonetheless, is worth 25% of what you paid for it.

AAAANNND with that, I'm heading for dreamland. Perchance to sleep.

Good night, Gracies!