Though I've dug into the possibilities of investing in STR's as well, it's a little less predictable and that might impede with your goals or timeline (depending how you answered the above).

Retail RE buyers might put stock in Zestimate, even though none of us on the investment side do.

Predicting the future is tough.

BUT....not hire investors wanting to take our money and invest in the stock market.Who should we look for ?

Gas fireplaces are fairly common in the housing stock we deal with over in Cleveland.

People with Jobs (easy to predict)  or people retired (not as easy to predict)  Few people will pay to rent something more than 30 minutes form their job.

It would be no different than you managing a portfolio of stocks for them as a note is a security.

- Due to the long distance and the HOA covenants, I'd have about ~19k in annual operating costs when I include both mgmt service fees and burden my ROI with the opportunity cost of not investing the stocks. 

However, 2020 can be turning point as will need to see economy, interest rates, jobs, stock market, unemployment, etc.Who said that you cannot sell at peak and buy again at low? 

@Reggie MaggardI have some cash and stocks.