You make revenue here and there but the goal is to generate enough in the winter to sustain all the expenses for the entire year. 

I don't know your specific market all that well but have you done some analysis on your ADR during the high season X your high season occupancy rate and determined whether taking lower priced slow season bookings vs letting your property stay vacant during the winter averages out in your favor?

Potential Objectives1) Invest in property for short-term rental, and then use the property ourselves in the winter. 

I plan to come a scope out locations/properties this winter. 

I suggest you wait until late winter to sell.

The winter months bring people from the south who want to see snow and plenty of outdoor and winter activities in and around the area. 

WE did a nice flip last may though in Winter Park that was a good one.

Aside from the standard BR/BA count and square footage, I always focus heavily on the listing pictures for any comps I pull in my area - finding a comp that's as close to your property's condition and finishes will give you the best apples-to-apples comparison possible.I also wanted to second @Tim Swierczek's input: nobody in Minnesota likes moving in the middle of winter.  

It doesn't make much money and I need to check on it for a couple of months every winter.

That fills your unit for the winter and buys you time to prepare for the next time.