"That said, the people who become the most trouble are often the ones you helped for as long as you could. When you finally stop, they'll hate you for it much more than if you were cold from day one."
This and what Ned J. said. I am about as bleeding heart liberal as they come....and my first tenant had so many excuses it was breathtaking. Paid the first month's rent to get the keys and then never paid full rent again, and it took 6 months to get him out, and our REALTOR got that first month's rent. (Never used a Realtor to find a tenant again either.) When we stopped accepting excuses, he lied to a judge's face and said we told him we wanted him out because of his race. (Judge logically asked "if they are racist why did they rent to you in the first place?" and then dismissed.) The morning of the eviction had a "heart attack" and called us "from the hospital". When we said we were moving forward he said some choice words and hung up. But 90 minutes later his stuff was all gone....pretty good for a guy who had a heart attack that day lol. I'd probably give your guy $1000--I'm still a bleeding heart...but I would not let him stay. They are never going to pay on time. If at all.