Yeah, the track record doesn't help.  Without public disclosure, a police report, telling the community the addresses involved, etc you pretty much have to put the responsibility for repayment on him.

With the unpaid taxes, unfortunately things like that happen easily if you don't plan ahead and have an accountant or someone who understands taxes to guide you.  Happens a lot to people running small businesses.  Can't really afford good advice, but can't afford not to either.

Not making up excuses for Jon, but the full list clearly shows that he's not a violent offender and probationary oversight is probably sufficient.