Newbie needs help with starting point in Chicago

[Daniel L.]

I'm a newbie that's in the learning and networking phase. I'm aiming to start looking for my first property next year and want to get some feedback on how feasible/realistic my strategy is. I plan on doing a house hack on a multi-family building (triplex or quad) in the Chicago area (northside, near west or near south) and I have $50k set aside for this with ability to borrow another $10k from an insurance policy. 

What do you guys think? Any suggestions, tips, or alternate ideas are much appreciated.