Come winter time, we have a feeling the house could be 80 degrees if tenants don't have to pay for it.

So I figure late spring, summer and early fall will be very conservative at 50% but wintertime will average out that because it will likely be less than 50%.

So, I didn't quite wait until winter time, which might have been a bit better from a timing perspective.  

Since we will likely be taking possession sometime in the middle of November, I am looking for advice on what to do in winter time.

I don't know how it is where you are from but winter time tends to be slow time for contractors therefor should help with the pricing.

Maybe it is winter time that makes it hard to rent.Sincerely,MariuszPSHeidi, let us know how your attempts are going

IE: Summertime, from the furnace, wintertime from the A/C.

When it comes to Columbia Falls, Coram, Hungry Horse, etc. they see tremendous activity in the summer, but kind of fall off in the winter time. 

It is the winter time, and it is 15F outside, and you are inside. 

no direct experience myself in Illinois,  but a mentor mentioned that evictions in the winter time will get delayed by courts due to weather. it's the same situation on my apartments in Indiana.