We had a deep freeze in the winter that meant I couldn't do a lot of work on the house because it wasn't insulated yet, and my plumber mid-job had a heart attack (no joke).

What does work is getting is going after the retirement market moving away from your winters.

I've found it helps to offer a boat for the summer, and ice fishing equipment for the winter months.

They will keep the AC at 68 degrees in the summer, and the furnace at 78 in the winter, because why not?  

You get in on a winter's day and start it up.

We're seeing this winter that the electric bill has doubled over what it typically is (it's now about $1000/month)–pretty much since the new unit moved in.

But I wouldn’t think areas like Ft Myers or Naples or Tampa or Southeast Florida would have much rentability in the summer as the winter is when people from up north look to rent vacations in Florida.

Need advice finding a contractors in my local area. Thank you,

I don't have to do that, but it lets me know if someone runs off in the middle of the winter and keeps my properties protected. 

I spent a winter in Colorado as a musher (dog sled driver) and living the ski bum life near Aspen,  but I knew I wanted to get up to Alaska permanently.