@Bryan Stengel, I think alcohol has been the tough one with the STRs, not sure about if you need license( hopefully someone will chip in ) , however there  always the liability part including but not limited to offering alcohol to people who are trying to quit etc.

It is quite the adjustment, but I LOVE IT HERE. 

I am in the Port Saint Lucie, Fl market and i have an airbnb that is doing quite well from an income perspective. 

The problem is, there's the giant water heater tank in the same corner that takes up quite literally a 1/2in too much space.

Cash flow is realistic, but quite frankly you make your money here in appreciation.

Who pays when the resident breaks the agreement and quits paying? 

I’m also not quite convinced that the property is unique enough to justify specific performance because it is typically only enforced when there is a lack of other remedies such as monetary damages.

., and I still love Cook County because I have a solid team and underwrite deals properly.I think @Paul De Luca nailed it on the head, though - it seems like you are quite risk-adverse, so maybe given your risk tolerance, it's not the best idea, but if it were me, I would not think twice about it, and find a rock start property manager who knows exactly how to vet tenants.

I'm not going to continue arguing with you about this on this thread because quite frankly nobody here cares if we are being honest.

Over the years, we have built quite a network of agents that bring us quality off market properties in the areas that we desire.