You need the lender's underwriter to approve your plan which would be typed as and amendment, the contractor may need to be vetted (license), this needs to be done AFTER the appraisal is completed so Underwriter can see what you are paying contractor for. 

The inspector didn't mention, but can I apply for a minor variance or zoning amendment instead of removing my tenant?

I will be amending my strategy to include some of the eastern suburbs (Mesquite/Garland).

However, from the sounds of it you would like to keep him in there and amend the lease agreement currently in place.

Property Tax increases:   According to Adam Schuster (June 15, 2022) amendment 1 would guarantee a $2,149 tax increase for the typical Illinois family.

Had the lease been amended or have you drawn up a new lease in the years after the first year?  

If you want to assign it, then an Amendment would have to be done that the seller signs that acknowledges the assignment. 

I would just say overnight guest more then  x time period have to be on the lease, since you have 5 bedrooms and you have 3 occupants I would be clear another roommate would be an amendment to the lease.   

The State is constantly updating and amending their law/s causing jurisdictions to change their ordinances about as often as we change our bed linens.

You can also fill out an amendment for specific issues not on P&S and turn that in to title co.