Currently I am house hacking as a mid-term landlord (list on Airbnb.. renting Jack and Jill upstairs in our home to traveling professionals) we are consistently booked and lots of inquiries.

If you understand it's largely an experienced play and won't go anywhere, there's certainly nothing wrong with giving it a shot. 

If you consistently analyze properties, recognizing a good deal will be much easier when it shows up.

Not sure if higher purchase prices/rates have created this boom or if it's that all the new supply of rentals in Chicago is aimed at top end luxury *$3000 1br type builds etc. but rents have shot up on the north side.

It may feel uncomfortable at first, you may have to find what works for you, but if you want to consistently find potential deals without immense competition it's likely where you should start.  

If you limit yourself to a zip code or two I do not see you doing consistent flips.

I literally sent him a screen shot of the sent bank statements I sent. 🤷🏽‍♀️ Im not the only person that has this issue.

You may want to use these as a starting point but @Bill Brandt's point about consistency is an important one to avoid a lawsuit.

If you consistently analyze properties, recognizing a good deal will be much easier when it shows up.

The city has been experiencing consistent population growth, which often translates to increased demand for housing.