New Hampshire would be much easier to start with as a it is very drivable and they have winter and summer travel seasons.

I am in Alaska, the dark winters just aren't manageable for me anymore so I decide for mental health reasons its best to relocate.

My plan is to monitor those rental listings during the fall and winter seasons, and see which units are more consistently booked.

Cross country skiing, snowmobiling, snow shoeing in the winter are popular.

Personally I'd disable, winterize, or remove it due to costs of maintenance.  

In other words, your price determines the perceived value in the guests mind, no different than a luxury purse fetching $1000 while another brand only $75, even though they are both made out of leather. 

@Mayur Dewaikar I don't have any good data on rental inventory but it's always slow in the winter.

The Fall and Winter months typically see less activity than the Spring and Summer.

Since you’re not looking for a profit it might work but probably won’t rent in winter.

I agree @Marc Winter you can request a raise each year.