With real estate, you have to make sure each property is functioning at full capacity or you’ll be losing money.You can analyze properties and be pretty sure (as long as you don't rationalize bad deals into good ones) what your numbers will be. 

I can see it as a corp retreat, maybe event space etc, but selling seems the best way to get out.But the best strategy is simple not to buy in an area where the risk is great enough to lose the STR aspect.

The other watchout is if you lose your job you are required to pay the money back quickly, like 30-90 days with most 401K's or the loan gets converted to a withdrawal that comes with tax implications and penalties. 

What is the point behind having paid off real estate, if you lose it later in life to oppressive taxes?

It's real estate in markets with population growth, it's pretty hard to lose money if you get an inspection and appraisal."....Wishful thinking at best when buying C/D properties.

Consider transaction costs as well as losing the principle residence exclusion.

THey are incentivized to take care of your property or they could lose their section 8.

I use a point system for screening; applicants get positive points for positive aspects, lose points for negative aspects, and I have a point threshold for each property. 

If I'm even able to find a buyer, I will more than likely lose every penny I put into it and probably have to pay.

Under Alabama law, that is a VERY dangerous play and you could end by losing money.You also cannot sit back and let him build the house and say "Thanks."