Hi Ben, I basically have a mentor and friend, who also happens to a realtor and quite a successful landlord himself, handling management for me (single family rentals), and he's been amazing.

Tenants are always given more than the appropriate notice for entry which is 48 hours in Chicago. 

I know a lot of ways to get that handled and quiet title with title insurance.

If the numbers look right based on what I feel I can reasonably handle, then I will buy anywhere.

My lease agreement states: "Abandonment" occurs when all of the following occur:(a) all occupants have vacated the Premises, in Landlord's reasonable judgment; (b) Tenant is in breach of this lease by not timely paying rent; and(c) Landlord has delivered written notice to Tenant, by affixing it to the inside of the main entry door or if Landlord is prevented from entering the Premises, by affixing it to the outside of the main entry door, stating that Landlord considers the Premises abandoned, and Tenant fails to respond to the affixed notice by the time required in the notice, which will not be less than 2 days from the date the notice is affixed to the main entry door.I know its early to worry, but if I does not hear from tenant in the next 3 days can I treat the property as abandoned and serve the notice?

Have a laywer handle it and do an eviction..

Homelessness is everyone's problem; the city is actively working on solutions, people may or may not agree on how it is being handled however better to be part of the solution!

His tone was probably less anger than frustration, but it's easy for someone else to mistake the two.I've been in the same boat, as far as waiting too late to get a trusted source to handle some work and having to rely upon that questionable resource. 

We have a property manager for another SFR in town and they said furnished rentals are too much trouble, so they won't handle it if we leave it furnished.

It looks like I just need to call an attorney and let them handle it.