This would typically occur only if you are over extended.  

Understanding STR regulations in a market is an essential "must do" when it comes to evaluating a short term rental.

He's essentially lost $150K.Run the numbers if he was renting it for 5 years (minus mortgage, property taxes, repairs, etc). 

Typically, we would only do an initial tenant screening at the beginning of the least. 

Not the typical 2 hour hotel room seminar with high pressure sales reps asking for credit cards etc. 

Typically the banks that say they can get it done in a few days I havent had luck with when getting creative as they underwrite the easy deals quickly.

Essentially ended up screwed out of a substantial chunk of retirement savings and left to find my own lender elsewhere to close the deal.

The better value add deals will typically be off-market. 3.

They usually sell for a really attractive price because investment property financing is (obviously) difficult, somewhat limiting the buyer pool to owner-operator small business owners (who in turn are typically great clients, as well).  

Also, what others have said, the personal touches on what is in your place (e.g. providing all the essentials instead of having people buy TP, coffee, shampoo, etc.) and the quality of those items (no tattered towels, stained sheets, etc.).