House Hacking in Chicago

[David Dyer]

Hello!

I am a total newb to real estate, pursuing financial independence pretty aggressively through index funds and a minimalist lifestyle (following the shockingly simple math, I have about 8.5 years left of working).

I found biggerpockets via reddit. I'm comfortable keeping my growth/appreciation potential on the stock side, but I'm intrigued by what I've read about house hacking. It seems like a dumb name for a very smart idea. I currently live in a 3-BR apartment with two roommates in Andersonville for $495/month, and after a bit of zillowing it looks like there is at least some potential to find a three bedroom condo where I could rent out the other two rooms without much risk of increasing my out of pocket monthly expenses beyond $495.

I work in Evanston and my social life is along the red/brown/purple lines, so neighborhoods I'm interested in are anywhere from Lakeview to Roger's Park.

I want to plug into the Chicago RE community by actually meeting people, particularly finding an agent and connecting with people who've done this successfully before.