Based on your post, it's probably best for you to simply not invest in Cook County for your own peace of mind.Sure, any tenant could stop paying rent and that risk is never zero.

If not, then what he is trying to do is to avoid his reputation going down the drain and lose any future credibility and trust in the future. personally I am just familiar with the basics of buyer seller representations in a general sense you will need a FLA Broker or Attorney to describe to you based on the documents you have if there is a Duty from the agent on this transaction..

Most lenders will vary how aggressive they will get based on the experience of the operator (you), but I don't know any that will lender to someone who's never done a spec build like you're contemplating.

Pick a lane based on your strengths and long-term goals.

This actually seems like a great scenario for a 1031 exchange based on what you've said.

My wife and I have obtained three traditional loans and one lease with the option to purchase, resulting in most banks turning us down based on debt to income (non-portfolio lenders). 

DSCR loans are based off of down payment, credit score and either actual or market rents so it helps to supercharge an investor's real estate goals and net worth.

I’m personally based in Houston, TX, and I’ve noticed over the years that a good realtor can do a lot more for an investor than just listing a property.

Permit eligibility is based on region (usually the west side of town) and density (quantity of surrounding STR's in the area) as well as percentage of landscaping and minimum parking requirements. 

The biggest key was understanding that It was more important to get on base then it is to hit a home run.