Last year, I had some issues with a contractor I hired to replace my sunroom.

The first trip around the Monopoly board ... you pick up as much property as you can afford and if you can't pay cash, you mortgage it.  75 of the last 80 years real estate has appreciated.If you can't afford it, the bank most likely won't loan on it based on their guidelines. 

Last summer, we were away for a few months and we made $25K from AirBnB on this house.

Cell phone photos and FaceTime calls can hide a lot of marginal quality work.  

Sounds like your tenant wanted to move and thought if they found a replacement that you'd be okay with it.Visit the property and get the occupants name, phone & email.

A majority of my buyers as of last year have targeted and purchased property in Winter Haven and surrounding areas. 

The thing with long term hold approach, there is generally a real boom that last 2 or 3 years every 7 to 10 years.

Given this was your home (ie, principal residence), and as long as you've lived in your home for 2 of the last 5 years, your sale is likely eligible for the Section 121 exclusion, meaning $250k in gain excluded from taxable income (or up to $500k in gain if married and filing jointly).

Inflation, rather Inflated prices over the last few years will stay up for a while. 

The GIS information for the parcel says that it was "illegally split" last year.