I'm not sure you can predict on time rent in one town vs another.Probably the main challenge would be PM if you want to use PM.   

Obtaining permit inspection from the city of Chicago is never predictable and your GC is not going to be able to predict the outcome any better.  

What do you predict it will rent for once you move out?

Generally speaking, I predict this doable but there is insufficient information here to determine if this is cost prohibitive. 

I just can't predict cash flows in these situations.

That will negatively effect the home values on the rise leaving a lot of people unable to refinance out of an FHA or in general to pull out any ARV cash.If it happens to where a lot of people are predicting some of these 203K loans that offer a 110% above property's "Future" home value.

You are trying to predict who will be a good resident and pay the rent.

The eviction ban ended a few days ago and here are my predictions.

Yeah, I do lean towards you being right, since the deed representing a parcel without regard to its use is really the financial instrument transferred, and whatever happens on the land arguably falls under that umbrella and can't really be separated out.

Right now even junk bonds are only paying 4% on average, so where is the seller going to get better yield elsewhere on a fixed income instrument that is collateralized by an asset they know and understand with an operator (you) that they know, like and trust?