I have a business once, the lease requires me to pay the property taxes, and the landlord had me set up as the payee with the city.

Also it's on the southside of the city so I'm kinda torn on this

Kansas City Investors & RE Professionals,What is your Recommended / Best Website(s) to Research Comps in Kansas City, MO Market?  

You should call up the city water department for the city you're looking at.

With all love for the city, we have the worst schools in the state, highest crime rates, highest property taxes (3.5% of property per year), highest income taxes.  

Being in Brooklyn and the expensive market here, I am looking in Union City/ West New York area.

It requires keeping up on the local area's news, attending council meetings, keeping up on what's happening in the city you want to invest in.  

Find out from them what areas of the city are more inclined to generate positive income.

Additionally, with the City adopting the IBC 2015 and inspectors becoming increasingly difficult to work with, we've labor costs go up and soft cost on the design & engineering side go up as well.   

I worry about city/government restrictions on short term rentals, but am not familiar with current laws in Chicago.