As soon as you start discussing your business practice and strategies with your customers (tenants), then all bets are off and you run the risk of Fair Housing violations. 

Of the options I’ve purchased, a majority expired unexercised, mainly because they were “flyers” for me on a bet on a beneficial event happening that wasn’t likely to happen.

It seems like you enjoy being active and using your hands so maybe the BRRRR method (buy, rehab, rent, refinance, repeat) is your best bet as you could save some money and do plenty on your own, you could also do a live in flip potentially and sell it or rent it out later.

This sale usually involves a monthly payment, which is on top of the rent.

so after reading all the posts, it sounds like his best bet is just to move on and walk away finding another place maybe coming back in future to keep contact with that person if he really wants that location… Correct me if I’m wrong, but my analysis from all this is that hiring a squatter would only be applicable in situations where the person who is occupying the residence never had a lease or contract therefore it is a rare circumstance where it would be a viable option. 

It took a while, and there were some fees involved, but it was totally manageable compared to what I would’ve paid with an attorney.

In fact I would bet not even the asset protection services who send you down these rabbit holes can and therein lies the problem...

However, in practice, lenders rarely enforce it as long as mortgage payments are current and there’s no added risk for them.If you want to avoid triggering the due on sale clause, the safest bet is to wait a few months after closing before transferring the deed to your LLC.

I don't think we will reach those lows again, but wouldn't necessarily bet against it, either.If you are skittish now, I'd get it on the market right now while there's still a season left, and price it to MOVE.  

I bet you could quickly get an idea about financing, insuring, and feasibility from them.