An additional thing that is slowing the deal down is they want to hand the house off in better than it's current condition.

Here is what I look for:-Overall condition of the complex? 

Honestly, with google moving to durham soon, regardless of condition id recommend you pursuing that deal. 

Do you all entertain sellers who do not want to discuss anything about the condition of the property nor do they have any pictures of the property?

Given that the property is ideally located and other economic conditions are right, you are bound to receive regular flow of rental income.

While I'd never play around with safety issues, people who rent well below market have to accept well below average conditions. 

It might make sense to search a little more west of Pilsen in Little Village or the Marshall Square area to find something in better condition at around the same price.

But in the case of having it fully managed by others, with a STR policy that requires $1M liability anyway, plus the management company's insurance, wouldn't most liability fall to them first as they're contracted to keep the property in suitable condition, then I'd still have pretty hefty coverage if something went beyond that?  

The house is in pretty good condition, though it's built 1950's, it's had lots of updates. 

I'm going to the Dec 10-12, 2021 Live RAL Academy training in Phoenix, anyone else going?