Simple: He hasn't lived in Chicago for a couple of years. What makes it worse are his attempts to retroactively re-attach himself to Chicago. In this case he wanted to kick out his renters so he could show he has owned a non-rented house in Chicago for the last year. He also amended his tax return, only changing the address to show him as a resident of Chicago. Somebody who knows he already has legal resident status doesn't do these things.