Hey Nate, welcome to the BP community and congrats to you for making the commitment to getting into real estate investing. There is no better way to jump right in than a house hack, in my opinion, so you're on the right track.
1. I was in your position a few short years ago. I purchased my first house hack, a 4-flat in Irving Park, and have since purchased a second 4-flat; currently seeking a 3rd larger investment. That first deal can provide a launch pad for rapid growth.
2. I'd recommend Landlording on Autopilot by Mike Butler. It's a bit dated from a technology standpoint, and kind of cheesy the way it's written, but it provides very simple methods for tenant management. If you haven't reached them already, give a listen to BP episodes 78 and 132 with Brie Schmidt. Not only does she provide a ton of useful info on house hacking, but she's based in Chicago so it's that much more relatable.
3. Like others have said, you need to reconsider the price point. $500k in those neighborhoods will barely get you a decent 2-flat. Not saying it's impossible. Like Joseph said, try to get into a 3 or 4 unit property if you can. You'll learn so much more managing more than one tenant, and cash flow trends in a better direction (although don't be surprised if you're still in the red).
Feel free to PM me with any specific questions or if you'd like to connect further.