Hello @Carli Schlaker, The best way to get started in my mind is the house hack, so good on you for looking into that to begin! Bigger pockets will certainly be a great resource for information for you and the calculators are a great way to vet deals I use them on all my deals so that can be tip number one. Secondly don't hold out for a perfect deal because they don't typically exist on their own, you have to make them. It's ok to spend a little too much money on your first deal its how we all learn what works what doesn't and where your specific strengths will lie. The MLS can be a hard place to find the deals you are looking for so it may be more cost and time effective to try reaching out to small multifamily owners directly. I don't watch the Chicago market closely because its about 2 1/2 hours from me and I'm currently self managing all my units.
I would also recommend the book Managing rental properties by Brandon Turner. https://store.biggerpockets.co... Its a great overview of what to expect finding and working with tenants. I think in the beginning you'll want to mange yourself so that you know how the process should work if and when you decide to have someone take that part over for you. This will kind of help you vet property managers in the future but also help with doing the day to day till you are ready to let it go?
I also use the Bigger Pockets leases which they have one specifically for Chicago. A Pro membership is less than couple hundred bucks and the leases alone are worth that.
Regardless take small consistent steps toward your goal and you'll make it just fine best of luck to you feel free to reach out if you have any questions!