Newbie in Chicago looking for advice

Thanks for reading! I currently own 1 rental house in the burbs that I used to live in with my wife and kids before moving to the city 4 years ago. My business partner and I own a successful executive search firm here in Chicago and are looking to invest in multi-family in the next 3-6 months. I have been listening to a ton of podcasts, talked to a realtor who I know that set up a search on the MLS. Also, my Dad is an attorney and does real estate/asset protection so I can get free legal advice. Would appreciate any advice on the best way to get started. We are interested in a hold strategy. Thanks, Brian