If my suspicion that he is a serial credit abuser is correct, then by the time he is a couple of years into rebuilding his credit, he will not want to risk having an eviction from you on his record, or a judgement in your favor.

But fortune favors the bold.

While not explicitly stated in the tax code that I am aware of, this has gone to court several times in the favor of the taxpayer.

They did you a favor.

In my case, it actually works in our favor, because nobody else can reach him too, so we are clear to have a shot at it.

There are too many factors that are not in your favor.

At the moment I think that buying all cash in and have capital gains in my favor could be the best step, thanks

Overall, if I had to pick which was tilted more in favor of the tenant, so would have to say MA.

If funds are going into passive deals, then you're probably looking at low/mid-single digits (unless borrower/deal is questionable) which isn't anything to get excited about.Have you considered partnering with somebody who operates and a more favorable market or looking at being a passive investor in syndications?

Carefully examine the experience and character of the sponsor and you'll tilt the risk curve in your favor.