If you constantly have to deal with applicants with evictions, you are in the wrong market or have the wrong property. 

I'm just curious how other investors are approaching these types of challenges in the current market and want to get some feedback on what I should be looking for when acquiring new properties.

The real estate agent throughout the sale process: "The markets have come down since you bought your property."

I estimate their combined value based on the current market to be around $900k.The goal would be to extract max cash out.

@Marcus Clouse..I'm not an expert in your market but do a good amount of construction lending. 

If the market value numbers above are correct then you def will have a nice chunk of change to play with.  

If you’re thinking about jumping into the Clearwater market with an STR angle, you’ll really want to dig into those local laws to make sure you're all clear.

Plus, you're talking a Brewery and restaurant; that will be a hard sale, unless the bank is local and knows your seasonal market really well. 

Unpredictable material costs, unpredictable labor market, unpredictable housing market.

Think markets likeCleveland, OhioCincinnati, OhioDayton, OhioToledo, OhioYoungstown, OhioCincinnati, OhioMemphis, TennesseeSaint Louis, MissouriIndianapolis, IndianaDetroit, MichiganErie, PennsylvaniaLouisville, KentuckyMilwaukee, WisconsinJackson, MississippiYou can win or loose in any of these markets.