House Hacking - Chicago

[Matt Ference]

Hi everyone this is my first post, but right now I am 21 and I am a senior at Northern Illinois University and originally from St. Louis, MO (go cards). I am playing football while getting my MBA degree. I plan on moving to the Chicago area after football to pursue a career in sales. I am trying to “penny pinch” right now for my first investment which will be a house hack.

I was wondering if anyone could give advice regarding 1. location, 2. where to buy from (wholesalers/foreclosures, or neither), and most importantly 3. an exit strategy with the main question being:

“Is it better in today’s Chicago market to continuously purchase and move into new house hacks and fill your personal vacancy after or to stay in a house hack for multiple years and continuously buy rental properties?”

My guess would be that it depends on your situation and the numbers and to maximize the cash flow, but I would love to hear other opinions as I am super new to investing!

I would also love to connect with as many people in the Chicago area as possible!

Thank you!