House Hacking in Chicago

[Nate Grabner]

Hi everyone! I'm new to REI and am looking to do a house hack in Chicago as an entry point. I've been renting with a couple roommates in Lakeview since March 2019, and work as a management consultant in the loop (or more accurately these days, from my couch). My current lease is up in March, with the option to extend month to month or move home for a few months after so I'd be looking to buy sometime early next year.

For education, I've read through most all the posts that seemed relevant in the Chicago forum here posted in the last 2 years, listened to many of the Straight Up Chicago Investor podcast episodes, been working through the BP Podcast early episodes, and just finished up reading Househacking by Craig Curelop and The Book On Rental Property Investing by Brandon Turner. 

As far as properties, Ideally I'd like to be somewhere where it's still manageable to get downtown or to visit friends in Lincoln Park/Old Town. I don't currently own a car so being close to the El/public transit would be great. I've been looking mostly in Humbolt Park E of Kimball and N of Augusta, Logan Square, Avondale, and into S Irving Park. I'd like to keep it under $500,000, and ideal building would be 3 units or 2 + an in-law/ADU - but would be willing to do a straight 2-unit if its in an area where I still think I could find a friend willing to room there.

My questions are, 

1) Is there anyone who has been in my position the last few years willing to network? I'd love to DM or hop on a zoom if you're willing to chat about your experience. 

2) Are there any other educational sources, specific podcast episodes, or books that anyone recommends? 

3) Am I being realistic in what I'm looking for? I've been watching zillow the last couple months to see whats out there, but would love to hear yall's input. Are there other areas that you think I should check out that still sound like good fits? 

Thank you all so much!