The roof is new and looks good on the surface, but all this added weight can't be good, especially in winter with the weight of snow/ice.

I will have free time over winter break and I am wondering if it is worth while to become a licensed real estate agent.

That had to be one high electric bill during those winter months.

Looking for a recommendation of a contractor who can secure the property, change the locks and do winterization.

We’re ready for another winter on that nasty road lol 

Not to mention your tenants wondering why the water bill is SO MUCH HIGHER in the summer than it was in the winter (they may understandably wonder if they are subsidizing their neighbor's extravagant water usage - and you know who they are going to be asking about that). 

Right now is a good time because most contractors are slowing down for the winter.

Thankfully winter will help slow that however that presents a whole diff set of challenges.

I usually just day trip for skiing, mostly to Copper or Winter Park. 

You also need to account for the fact that we are in the Fall/Winter and there are less active buyers looking for a home.