These can collapse or roots can enter them.

Of course there are other factors such as age... if it was constructed with clay or cast iron tile then most likely tree roots have destroyed it, vacant or not.

I would make sure you have a tenant who is either employed or on the way to employment very quickly and who is rooted in the community. 

At the root of it, I believe you are undecided on your market because of the lack of knowledge on those markets you're looking at.

This is going to sound like a bad soap opera, but here goes...What happens if you have a property sold on seller financing and the buyer uses it as a rental.

Quality Linens, soaps, etc. 

I have personally done both sides of things; ran PM biz grass-root's, and ran PM brokerage in a franchise system, a big BIG name one. 1 universal truth that stands in BOTH is your primary existence as a PM, franchisee or grass-root's, is that your a full-time "vanguard" of defending against the "WTF's" and in being a "Fire-Fighter" putting out the "fires" of the various "WTF's" that happen.     

I am curious as to what root causes have decreased the Chicago inventory more than other major cities. 

It has taken in water in the past however the root of that issue has hopefully been addressed adequately at this point. 

Anton Ivanov Thanks for sharing and I’m rooting for your continued success.