You are probably priced too high and think your renovation is better than the public thinks it is price wise.

It was not a fast job and they overloaded the back of the pickup quite a bit weight wise.

It seems you selected your markets wisely and have actually been able to realize gains when you sold. 

As the scripture states, "A wise man leaves an inheritance for his children's children."

@Dan AshleyYou’re wise to be looking for ways to turn rent into your own equity.

Choose your markets wisely to invest in.

The thing I've found with tiny houses is that the outdoor space has to be amazing (design and view-wise), or it struggles.

@Kitty Walker- As an investor, I've refinanced multiple Padsplits and co-living properties (where we go direct to tenant without Padsplit), and I generally agree with your last statement, with some caveats:- if the renovation is done well, the appraiser may not even say anything that would indicate it is an "abnormal" SFR (has happened multiple times with me)-the investor may be wise not to make the house crazy- just leave a nice open living room, put double doors on the dining room so it can function as a bedroom now but be easy to convert later, etc.  

As a fellow Northerner, I tend to buy in the Southern half of the US for 2 reasons:1) you get much higher year-round occupancy rates in the South & it’s simply tough to earn a good ROI in the North if your place sits vacant for a big chunk of the year2) Culturally, the Southern half of the US seems to be a lot more accepting of STRs regulation-wise.

While the repairs will temporarily affect rental operations, the long-term tax advantages from depreciation could help recover some of the initial financial outlay.In terms of negotiations, it would be wise to push for a larger price reduction instead of accepting a cashier's check, given the magnitude of the repairs and the expected loss of rental income during the downtime.