To me, one is an act of kindness, the other would be funding what equates to a gambling addiction.I'm glad I'm not in your shoes. 

He became a devout born-again, ditched all his gambling buddies and started spending all his time in church.

The other tenant I’ve talked to via Facebook messenger multiple times, previous owner said that was the best way to get in touch with him, which I’m not thrilled about that as a communication tool, but I’m navigating that avenue as best I can with him.

I see it as a form of gambling. 

However, that's a gamble and not a good business model afaiac.

If they only had a M2M agreement, this won't thrill them, but they should have realized it could go either way - that either of you could end it after just 30 days, with 30 days notice.If they had a year lease, they won't be thrilled either, but they can never then claim that you held them to a year lease, when they were encountering problems, etc.Whenever I invoked the "happy clause," my complainers usually were shocked, but then shut up and quit complaining.  

A 720 probably would have got me a slightly better rate, but I didn't want to wait and gamble with the market if rates went back up higher.

Come on, you're smarter than this.This person might be a great person to have play dates with kids - but still be a terrible gamble as far as a tenant in your investment property.  

Before I just chalked it up to karma, if I really didn't want to pay for a lawyer, I'd at least take the gamble of representing myself and bringing my 3 witnesses. 

You're gambling for a chance of appreciation with lesser cash flow.