I even try to unsell them on the business by sharing my financial losses, litigation,  market shifts, permit purgatory, shady contractors,  clouded title issues,  paranormal activity, squatters, mold, etc.

It’s just not that common even though that is one of the main things talked about. 

Even if you take the $250,000 the realtor mentioned it would sell for as your basis that would mean you're looking at an $80k gain: 380,000 - (250,000 + 50,000 improvements) = 80,000Since you want to buy a nicer home for your mom, a 1031 exchange may not be applicable if the new property is intended for personal use, as 1031 exchanges are for investment or business properties only.

The people with single rooms even paid a bit more.

Even in the long run.

.: Thanks, Dan, but that's not helpful since it (a) involved a car, not an investment property, and (b) wasn't even used.The advice from almost every investor is to protect your investments with an LLC or umbrella insurance.

And while a 1031 exchange isn’t an option, some people explore alternatives like installment sales to spread out taxes or even tweaking the investment structure so your returns are treated as interest instead of equity.There are definitely some creative strategies out there. 

I understand that they would all be considered unrelated even though two of them are cousins. 

Normally the escrow agent will want mutual sign off even if its clear the contract terms indicate one party should be awarded the escrow funds.

Even if you haven't been in this kind of setup before, I am curious to hear your opinion.