Try to catch a “wreck” before it turns into a total wreck.  

More often it's just a train-wreck waiting to happen.The biggest hurdle (other than the potential liability, including defense costs when things go south, regardless of what the seller would sign off on prior to or at settlement) is the requirement that HOI (hazard insurance) continues to protect the lender and owner. 

There are so many facets to this I've been in a tailspin and a wreck.

Of my older MF rentals (2016) one place went from $515 a month to $625 a month now, which is cool but the value-add with this latest buy is what has really given me a push as the place was a wreck (it's nicer now but I'm not yet done). 

I know it seems to good to be true though, haha Well then what I would say is build some reserves and get some ground underneath you before venturing into something that could wreck both your business and your relationship.

Ideal renters for me would multigenerational families of means looking to book full weeks in the summer, have a great vacation without wrecking the place, and come back year after year.

Second caretaker got drunk at 1 pm on a Tuesday and wrecked that same truck.  

"Hey the house is a wreck".....?

It's incredibly uncomfortable, nerve wrecking, scary, and when it rains it pours.. this is your monsoon. 

If they are unwilling to buy in a benign economy, there is no way in heck they will buy when the economy is a wreck.