Advice on first investment property in Chicago

[Mark Gast]

Hi, I am currently searching for my first investment property in Chicago and as far as I can tell it is hard to generate cashflow in the city.  It feels like most properties in the more 'hip' and even 'up and coming' neighborhoods have already accounted for significant appreciation in the asking prices.   I have lived in Chicago for 3 years now and I know that need to do more research so it would be greatly appreciated if anyone can point me in the right direction.  For what it is worth, I don't have a ton of experience in real estate.  I have owned one investment property in Michigan but currently I just have my primary residence in WP / Bucktown, no rentals.  

Also, I would love to hear any opinions on a property like the one linked below.  Ideally, I am looking for a cheaper multi-unit like this or I would be willing to start out with a cheaper single unit (<$300K) if it can generate cash flow.   

https://www.redfin.com/IL/Chicago/2049-N-Kedzie-Ave-60647/unit-1/home/13418191