It's technically a criminal misdemeanor so jail is a possibility.

Not saying that's the case, but there's something called 'Toxic Giving' which causes people to continue performing the same behavior to a point where they're absorbing resources that could have been used to help people who are truly in need.

In general, applicants are on their best behavior right before they sign.

But I'm a little freaked out by his criminal record.  

I "pre-screen" tenants all the time by asking them about their income, Landlord references, criminal history, etc.

Venmo and Zelle haven't had a huge crackdown on this kind of behavior yet, but they could at any time.

The Application gives you background, credit, eviction history and criminal checks. 

That's what happens when interest rates are at 8% and purchase price/gross yields haven't adjusted.The gross rental yield is only 9%, coupled with expenses it's less than the cost of financing - hence you earn yield by removing the cost of financing with cash.High rates encourage this kind of behavior (holding cash or using cash to cut interest expense). 

Friendly letters do not change behavior...Invoices do.

Have you done a criminal background check?