@Kristin Vegas - If you are buying in Chicago proper, be sure to become familiar with the landlord tenant ordinance which is specific to the city. https://www.chicago.gov/city/en/depts/doh/provdrs/landlords/...
There is a good stock of multifamily housing just west of the city if you are looking for a more suburban feel with better schools and policing while still being able to get to the Chicago city center within 15-20 minutes.
If you are considering house prospecting sight unseen, I suggest to use an investor centric broker who has experience with detailed virtual tours and rehabs. For reference, my tours of a single family home usually encompass 200-300 photos.
Chicago and it's suburbs are notorious for multifamily zoning and illegal units issues. Particularly with an FHA loan, you might find a home where the parcel is zoned for 2 units, but has 3 units which is legal-nonconforming... but then your loan officer will only count two of those units of rent to qualify for the loan because one is nonconforming. In Chicago, many times on the MLS there is a garden or attic apartment listed as a 3rd unit on the listing, but when the zoning certificate comes back from the city, it will only specify two units. That would put you at a huge risk if it were ever to be inspected by the city as they would likely force you to de-convert that unit.
Most suburbs here have city inspections required prior to the sale taking place, Chicago proper does not.
I have some strategies to BRRR quicker than 6 months if you are looking to move quickly. Feel free to reach out.