The key to longevity in this and any other business is to make sure that you are always delivering more value than you are extracting, and value has many different forms ... if you do that consistently for long enough, then you will not need to search for business or deals, because they will find you.

Just wanted to get some feed because it was my first time hearing of such a strategy.

"Wali says his properties see a lot of “anti-establishment” foodie millennials who seek under-the-radar areas that haven’t been displayed on their Instagram feed.

@Kent BaltareI agree with @Rob Javins that the area consisting of Gatlinburg, Pigeon Forge, Sevierville, and Townsend, TN may be a great fit based on what you described.A client of mine who owns some vacation rentals in Gatlinburg also owns a few in Myrtle Beach, South Carolina, and he has told me those do very well.  

That way, I could validate that I could consistently cover worse case expenses AND save money for the investment at the same time.

Yes - Zillow is consistently wrong.

He has a contract that says he makes $20,000 per month even if he just sits around doing nothing, and gets a crap ton of bonus on top of that, that I can prove he's been getting on a consistent basis for over a year.

Be patient and consistent.  

It would be reckless and irresponsible to assign a value on a refi that is consistent with the highest priced sales in the neighborhood.  

They co-mingle funds, they do not maintain clear and consistent lines of responsibility, etc.