I am making a list of "Safety rules" for tenants to get their acknowledgment via DocuSign  before the winter :)))

First, our winters here in Boston can be rough - and tenants can be very sensitive to issues due to lack of insulation (cold spots and drafts) Second - big picture you may not have this property forever and will need to insulate before selling because that will impact how a potential buyer will value the home.

I disagree with @Marc Winter.

It sounds like you need time to prepare, moving is tough.I have not been to Montana, but hear winters are extra cold and snowy.Have a Merry Christmas and Happy New Year while you take your time getting ready.My $2.

I only run the heat a few times a winter.  

This past winter two of my friends were talking about selling as one wanted to retire and the other wanted to move in with his significant other.I advised my friend in Seattle to get out in May which he did.

Hey Ali,The winter months can be a more difficult time to find a renter.

Foundation issues are widespread due to faulty drainage and the cold winters.  

We also bought one of those Pesticator repellers, so we'll see what happens this winter.

Unlike, Norman (Oklahoma University is located here), Winter Garden (University of Central Florida is located here), and Boerne is a military area.