Rise48 seems to be a good operator. 

I am open to meeting like-minding professionals who could give me some good insight on my journey.

The issue I could see with this is they have a 6 mo lease and we didn't state in the lease that their primary heat/ac controls are with the mini split and it does a good job of heating upstairs but the downstairs still gets heat/ac from the other unit.

Most investors who focus their underwriting on successfully completing the BRRRR method ignore the fundamentals that are most indicative of a properties long term success.

There's a very good chance the issue(s) you face have already been discussed and answered.Ask questions in the appropriate forum.

You'll need to get good at analyzing rehab costs and predicting after-repair value (ARV) to ensure your margins are solid.To get started, immerse yourself in real estate education—read books, listen to podcasts, and use BiggerPockets to connect with experienced investors.

There is a lot of good feedback here already.

And as new investor, you have to expect to be charged more than a builder, but armed with a little knowledge you can get a better price than a homeowner and still allow the contractor to make good money.For most construction work materials times two is a good guesstimate, so about $6k is likely a good price. 

@Luke Stewart as long as you do 32+ days, you can rent on Airbnb Long Term in the city of Chicago. :) That's what I do, and it doesn't require any permit, registration, or license from the city.

Yes, it is good to get a deal or two under your belt.