I personally think being a landlord in Chicago is easy and I have never had an eviction. 

Think About Future Value & Target Demographics•Check the average income levels in the area.

Do you think this issue is specific to banking services or what do you think is the root cause?

I don't think that's true.  

Think multi unit residential, commercial properties, or purchasing houses “subject to” existing mortgage.  

Hi @Sean Leahy - good direction, I've never considered this but now that I think about, whenever I've had some random rental/sale listings I've been approached by brokers who said they represent folks that are part of the insurance company's claim management process (e.g. their house burnt down due to an accident). 

I came across some critical information today that I think is important to share with you:In the aftermath of the LA fires, it has become evident that some homeowners’ insurance claims have been denied or disputed because the property title was held in a trust, but the insurance policy was under the individual homeowner’s name.This serves as a valuable reminder to review your insurance policies and ensure that the ownership structure on your property title matches the named insured on their policy.

I can think of probably another 100 questions, but you get the idea.  

Current owner is willing to break even on the purchase price however, in my opinion I think he should consider 5 or 10k less then the purchase price considering the amount of repairs he neglected over the length of ownership.

Before you think you're getting in for zero down, have you asked what kind of cash reserves you have to have to qualify for the loan such as X number of months rent, and X number of months taxes, and what about insurance are they going to require you to buy one years of insurance or something.