It is challenging in the winter months as people tend to focus on the holidays, shopping, dinners, parties, etc.

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.  

I drive a Tesla… it’s a really fun car… but has so much acceleration you can get yourself in a dangerous situation if you don’t respect its capabilities… especially as a new driver.  

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?

I suggest you wait until late winter to sell.

Honestly, the first question that you and your wife need to ask yourself is whether this is primarily an investment or primarily a house for fun. 

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

Quote from @Derrick Lewis: I looked up NY state law just for fun and found a good list of recommended practices.

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

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