Getting a start in Chicago

[Devin Drowley]

Hey Bigger Pockets,

My girlfriend and I have been building up the courage (and knowledge) to get started in real estate investing for the past few months. I recently found Bigger Pockets and have loved reading the forums and listening to the podcasts, but I figured that if I just kept reading and listening, I'd never get started!

I'm an engineer and work up in the far Northern suburbs, and Steph is a teacher that works at a school in the North of Chicago. We have a few months left on our lease, and want to find something in the North side of Chicago or the Northern suburbs.

From everything we've read and listened to, it sounds like a great way to get started is to "house hack" with a small multi-family property. Do you have any advice for first time property investors interested in starting out with buy and hold properties? Is that a good way to get into investing? A few of my friends that invest in real estate have told me that flipping is the best way to go, but buy and hold just seems to make more sense to me (and line up with our skill sets..).

If anyone has a good investor-friendly real estate agent that is familiar with North Chicago and the Northern suburbs, I would really appreciate a referral.  Does anyone have suggestions about how I could get some hands-on experience or meet others to learn from?

Thank you for your help and all of the valuable insights I've already been gaining from this site!

Devin