Chicago has so much red tape around it and if you aren't going to do it at scale it honestly isn't worth the time.The market is giving you your answer on the pricing...it's too high with current conditions. 

Red flag? 

Hopefully it's walkable to the Fresh Market, great restaurants, and the Red Line.

Putting property in LLC when one has loan, is either not possible or will raise red flags with the loan company.

I attribute this to a consistent flow of out of state buyers (we are a red state and are a haven for political refugees ;) and we always have low inventory.

I bet these guys are Pace Morbid students and are shot gunning all over the US.. the big red flag is the statement  ( we will return the property in the same condition or good condition) that is just plain not true if the deal turtles up you will get a home that has been a rental and probably needs  a full rehab.. 

When thinking it over there was a couple red flags.

This should be viewed as a red flag as they are often the GC's who are taking from one job to cover another and that's when everything tends to blow up. 

Any red flags that steer you away?

Do infra red thermal cameras work for that?