The bleeding is now over and you can move on with a quality tenant that will provide you the cash flow and property respect that you deserve. 

A tenant doesn't qualify for a S8 voucher by making good financial and life decisions, so what quality of people do you think the system is dealing with?

We've had clients over the years who love Bronzeville & Hyde Park and have purchased large buildings with condo quality finishes or updated the buildings & are cash flowing while living in the building.

Whether or not you get the high end of that dollar amount, is based on the quality of what you are renting. 

I’ve had to rent in the offseason before and have gotten quality applicants but it does take longer. 

In my experience, Section 8 tenants are low-quality.

If they agreed to that, then the clause appears to be fulfilled assuming the lessor approved the quality of work.The entire clause is kind of sorry in the way it's put together and reeks of amateurish property management by an owner.

To determine the quality of a property requires to evaluate all of its return as well as potential return.  

Review the quality of the tenant base (do they have a history of paying on time, what were the original screening criteria, do they have applications on file).

Are their listings detailed with good-quality photos?