You can probably get some snow bird coverage through winters in your area.

Though, I don't suggest solar heating for your pool, it's typically only good for about +10* over the outside temp, meanwhile I can heat my jacuzzi on electric in the dead of winter to 104* in about an hour and control the temp from my phone. 

A second wave of infections is predicted for the winter, which could mean another lockdown.14 If you wait, you might miss your window of opportunity.How long do you plan to stay in your new home?

The property is in a growing, historic city with low seasonality (summer always does better, but still steady business flow in the winter months as there's year long activities).

It's a seasonal business, so over the winter I took the course, I passed the course on April 1st right before I had to devote some time to getting my seasonal business up and running for the new season. 

I've heard great things about Pisgah Forest, Cullowhee, Cherokee, and Tuckasegee.

@Esteban Carrera No need to be concerned about pipes freezing now in the summer but I would reach out to him and let him know your concern for the winter months coming up.

But what about the winter months? 

Am I missing the forest for the trees though in terms of cash flow?

I think that is lowest AC can be set.Hot tub, 240vac (has some age on it)2 80 gallon commercial water heatersWell pump, 2nd pump for holding tanksTons of LED lights and ceiling fans.Large windows facing the mountain views.Have you invested in things like Geothermal heat pumps, solar cells, window film to filter some heat( helpful in summer, harmful in winter), solar cells, etc?