You can't avoid that, but a good mentor/partners/coach can mitigate it.

If you balance the portfolio with say 80% cash flow positive and 20% on the extreme ends, you'll mitigate the risk of losing your shirt should the prices drop as your portfolio will be self sustaining. 

While it is also true that Chicago leans tenant friendly, you can mitigate a lot of that risk by investing in areas that have a stronger tenant base.

But inexpensive and will mitigate your risk.

I have a secondary residence home insurance on this house and getting claim back for the mitigation/repair work.I have this house on Airbnb for short term rental.

I've thought to mostly stay away from condos but I like how you are mitigating the risk of them by buying up so many and being on the board of directors.

Auction.com is hired by banks to sell assets to highest bidder through quasi on line auctions.in some states LIke Alabama they are actually the criers at the public court house auction.. if not sold there then those assets are brought into the loss mit departments then listed with auction to be sold on line at some point in the future.I like it as they require actual money to buy this stuff as in you need healthy deposits and REAL POF's and you can't assign contracts etc.. so it mitigates competition with the no money wholesalers that are out there by the millions  LOL.. 

"The best laid plans of mice and men""Patience is a virtue"First I may suggest to envision your end game, to own a smooth running, cost mitigating and profitable MFB( multi-family-buliding), MRB( multi-residential-building) or could it also be a MUCB ( multi-unit-commercial-building)?

In your case you would have to be able to say that you had intended to build this house and hold it but there are now substantial mitigating circumstances you can demonstrate for why you are selling it so quickly.In general new construction and fix n flips do not qualify for 1031 treatment.

You need to establish a written history documenting this problem and your efforts to mitigate damages.