Trying a new hand in Real Estate Investing in Chicago. Ideas or pointers?

[Josh B.]

I had a previous rental back in Michigan that helped generate a fair amount of extra income. But it was more of a learning experience though. I want to take the plunge and buy again. 

I want to head in a better direction here but I have heard bad things about buying and renting out in Chicago. Anyone experienced or have any recommendations? I heard the city is EXTREMELY pro renter and somewhat give the finger to the landlords. Would I be better off looking to buy a property outside of Chicago?

I have roughly 20k to put into a purchase. Ideally I want to do 2-4 unit building and build on this. Thank you so much for reading! ~Josh