We live in Iowa where there is always ice around in the winter time.  

If you do decide to sell and can hold off until March, otherwise you're selling from a position of desperation since it's winter time.

HVAC contractors do not lay off in the winter time there is no supply of technicians out there but there is plenty of demand so we will pay our people even if we don't have work to make sure that we don't lose an employee and I'm sure other contractors are doing the same thing.

Any special rules for landlords in winter time in Chicago, Cook County, Illinois like ashing walkways or puting salt on those?

I will definitely keep in mind prices are lower in the winter time. 

I just had a similar issue, previously vacant propety with new tenant moving/moved in.Usage (in gallons) over last few days: 1,200 then  7,200 and finally 5,500.This is winter time in Midwest so no pool and tenant is in process or moving in so not squatters. 

Slim pickings during the winter time

So, to still buy in that winter time frame and fill in the empty renting space in between, would it work to just airbnb that time period?

Finding good tenants in our area during the winter times can get tough. 

It got rented in the winter time after about 3-5 weeks on market.