Short-Term Tenants...Not So Short-Term

[Bradley Levy]

Hello All,

I'm hoping for some advice.  My partner and I purchased a Chicago two-flat back in December that we owner occupy.  It took us 1.5 months to rent our other unit at a price lower than we wanted.  I attribute this to the lull in the rental market in the dead of a Chicago winter.  As a result, we took on a "short term" tenant that had a 3 month lease with a month to month extension while their house is being rebuilt (had fire).  We are now heading into our 9th month and are quickly exiting what I understand to be prime season for renting in Chicago.  I'm torn because I don't want to kick these people out but I don't want to screw myself where they up and leave me in December.  The logical answer is terminate the lease and the emotional answer is to let them stay.  I'm  wondering if I can find some common ground here.  Can anyone speak to when the Chicago market takes a dump for the season?  I appreciate any opinions, input, or anecdotes of similar situations.

[Kimberly H.]

Hi, I'm in the Chicago suburbs. May through July is prime time. It's even noticably harder in August but I am in the suburbs renting a house; people with kids want to get moved in before school starts. I have been able to avoid putting a place up for rent in the winter but from what I've seen in MLS it takes a long time. If you give them 30 day notice today, is the place in showable condition to start showing it right now?? Or is it a total nightmare with boxes all over? I only show properties for rent that are tenant occupied look decent and don't have tenants that are mad at me, otherwise I think it's more of a turn off. If you have to wait until Sept 19th to list it...you better list it for a real attractive price, like $100 less than if you listed it in the summer, to get it rented before the holidays hit.

 If you are to nice of a person which it sounds like you are, hire a management firm to manage your building, those that are to nice will get taken advantage of and taken to the cleaners in this industry.