This is for sales and if you need to hold for awhile due to a market change in pricing.I did a flip in an area that was a secondary market, and basically lost a couple thousand on the flip not following this rule of thumb..

We’ ve made some research and  spoke with couple of them however based on experience from investors on the ground we would like to hear from you and  any advice would be greatly appreciated. 

I like the fact that the price points are lower than most other markets and that the city is home to Norte Dame University.

It’s probably more than $5k your realtor has offered to take. 

. - The insurance industry like many others (including our industry of home remodeling here in Chicago) has escalated exponentially in cost.I've got several local Chicago brokers I can share with you, but I think no matter what your rates & premiums have probably gone up...I will send over a couple of contacts for you.Just curious, what neighborhood of Chicago is your building in?

Invest in something closer to home.

I too usually tell people to start with more of a turnkey property or a light cosmetic rehab.

We sell more multifamily than anyone else and come across quite a bit off market too!

then when it's finally rented, in that first month your rent is $14 more than your expenses. 

Buying 2 investment properties would likely bring in more revenue and equity than renovating an ADU.