@Eric M. let me be more clear of my position. There are parts of Chicago specifically in the South that are seen as very trivial from what I hear ie. Englewood. Of course you living there provides way more insight into the current economy and personality of the area, than anybody who has not experienced Chicago and is just talking. Now I don't know exactly where you live outside of downtown, but I am just referencing South Chicago zip 60636 for example.
To answer your question, about why choose a place with a stigma that I barely know..... why not is my response. I am a newbie investor asking questions, trying to test unknown waters understanding that my local investment area downtown DC, Arlington, Alexandria, etc. is very pricey to start. I have family in Chicago who know of my real estate pursuits, and so when they reach out to me saying to check out the Chicago area more, then I will look into it. I have not blindly bought property, just getting informed and reaching out to local investors, attorneys, and brokers such as yourself.