Buying in Chicago for long term? Or should I rent?

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 Hello everyone, 

My job is taking me to Chicago this winter. I’ve never lived there, and I could love it or hate it - hard to tell  from previous visits.  I anticipate that I will stay there for 1-3 years, depending on whether I like the city.

I am considering purchasing a condo for myself to live in which I would rent out later on down the road.  I have 20% down available and ready to buy a condo in 250K range.

A couple questions come up though: I heard that Cook County is not landlord friendly,  and dealing with a rental later on might be a pain.  So for the short term it might be worth just renting. On the other hand, a rental downtown would cost me about $20,000 for year. That’s a lot of lost equity. 

 The bottom line question is, given the situation of uncertainty whether I will like the city or not and the reality of being a landlord in Cook County, would you recommend renting or buying a condo and renting it out later?