My concern would be he is too far in the red for even that!

If the tenant causes trouble, he will cause trouble no matter what contract you have.

The property is cheap enough but I am concerned with buried stuff if it turns out to be buried drums of waste oil could get expensive to clean up.

Not your concern as far as the legal stuff, although I'd want to know what the issue is in case it could have some liability for you in the future (drugs, illegal home business).

However, if you end up determining that the stove is not working as a result of some sort of negligence or damage caused by the tenant, then you could try and bill them for the repair cost.

We have been buying investments since 2008 and have built a new business around managing our own properties cause I don't think I could trust anyone else to do the job.

I think this idea is way outside of the realm of the concerns for the average investor.

I'd definitely not send him checks, end of next month he needs a license to service OO consumer debt, if he's not a broker he's probably not a servicer would be my guess, but requiring pre dated checks is an issue as well.You'll need evidence of his requirements, not phone calls but you can record calls if you comply with state law concerning recorded conversations, you need to see an attorney for that, a prosecutor may assist you.

If you are concerned with him outright defrauding you, then you shouldn't be doing business with him.

That return improves when you buy below market value and that takes care of some of your concern about a market downturn.