Problem is the upstairs gets super hot while the downstairs stays colder in the winter.  

These properties are located in Milwaukee, Wisconsin in a C neighborhood and finding a renter in the late-fall, early-winter months could be difficult.

We're entering the winter sales season are you prepared to hold until spring?

But in this area "irrigation" water is free but it gets shut off for the winter in the middle of October.  

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

I like m-m's and have a few that have gone on for over a decade that way.Here in the north, coming up vacant in the middle of winter is never a good idea.  

I live in Oak Forest and there are several of those in the area along TC Jester and also along Pinemont and 34th St.

Some landlords tried including electric, gas, cable, internet with the rent to the students... students loved it, landlords got clobbered, because students were now leaving all the lights on, their windows open in the winter with the heat on, etc and the electric/gas bills skyrocketed which now the landlord was paying.  

You are still allowed to reject that unauthorized roommate if you find criminal or other negative findings from the screening.If you decide to approve the new tenant, just draw up a new lease for a 1 year term (or your choice) with the new rent and make sure all roommates are included on the lease. easier that doing addendums for rent and roommates etc. and you get them to commit to a new 12 month lease so you dont risk move-outs in the middle of winter.

One thing to consider is that I don't believe it is technically legal to VRBO/AirBNB. http://kutv.com/news/get-gephardt/air-bnb-rentals-...I did have a friend who used his house as a winter ski rental and seemed to have good success with it.