House-Hacking in Chicago

[Matt Byrne]

Hey everyone,

I’m in the process of getting my first real-estate deal planned out, and have decided that a house-hack makes the most sense. I’ve heard time and time again that it’s a great way to get introduced to the business, and it will work well for my current way of life. Part of finding the right deal, from my understanding, is choosing a market, learning as much as possible about that market, and making connections and getting out there to find the properties. My business partner and I have been analyzing different areas in Chicago, and we are not quite sure where we want to invest - the city or the suburbs. Cash-flow is the top priority; appreciation would be nice. There are cases for both locations, so I am wondering if any of you have experience house-hacking in Chicago (or the suburbs) or investing in multi-family units in these areas. Are there areas you have had particular success in? Areas you would avoid (that otherwise would be considered 'fine' or 'safe' neighborhoods by non-investors)? Would you avoid investing in Chicago all together? I would love to hear any insights, and always appreciate your sharing of your knowledge.