Hi @Donald446 - I'm applying for my first license for a unit in my 2 flat (I live in the other one). Adjustment was rejected so I too am waiting for an appeal date. I can't answer your question but as licenses need to be renewed annually, I'd assume they could refuse every year???
We too are losing income, so I have rented it on the "mid-term" market. If a rental is more than 30 days, its not classed as vacation rental and so no license in needed, as per City of Chicago Code.
Let me know how you get on.
Bruce