People will rent homes in that area because they cannot yet afford to buy, but hope to buy a newer home in the future and keep the kids in the same school system and around their same friends.

We have a real estate agent and investor friend, but not sure we’ll work with him.

It tends to hide marks better.Walls: Neutral tones like SW Repose Gray, Behr Swiss Coffee, or Moore Classic Gray are renter-friendly and modern.Trim and Doors: Use a crisp white like SW Extra White or Moore Chantilly Lace.Accent Walls: For a touch of style, consider an accent wall in soft blue-gray. 

The energy in person is different for me, and I've made some of my best connections and friends at Chicago meetups.Here is a list of the Chicago event from BP: https://www.biggerpockets.com/forums/521-real-estate-events-...I also have a list of ALL THE CHICAGO MEETUPS that I am happy to share with you. 

To me, PML is a friend of a friend or an Uncle or a co-worker's father. 

Do you know the area very well or have family/friends that live in the area?

My friend @Julio Aguirre is doing quite a few flips on the south side of Chicago right now.  

If you’re open to short term rentals, there are lots of places across the state that can really work.I’m a local investor-friendly realtor and work with both long-term and short-term rental clients.

https://www.meetup.com/dfw-flippers-and-funders/Also connecting to investor friendly local  realtors will help as they will themselves do flips as well

They are inherently more expensive than conventional financing and each DSCR LENDER has their own guidelines.