@Inna5 There are a lot of things at play.
Firstly, I think many Alderman and residents, especially on the North Side, are fed up with Airbnb "party houses", and are using that to have the City crack down hard on hosts where parties may have occurred, even if the host was unaware of it. That seems to be resulting in a low tolerance for any situation that exists outside of the letter of the STR ordinance. Some of those Aldermen were vocally opposed to Airbnb in their wards right from the start, and are looking for any opportunity to revisit and tighten the rules.
Secondly, there are things in the ordinance that make multiple registrations in one building complicated.
- if one is incorporated as an Inc or LLC (not a natural person)
- if one hosts in a single family home, but it is not the host's primary residence
- if it's an apartment or condo building with limitations
Thirdly, since City offices have been closed due to the pandemic, the usual appeal and review process has, I imagine, been largely stalled.
It seems like the situation of having multiple listings at one address automatically gets flagged for administrative review.
I wonder if you can wait until City offices have opened up, and then revisit the appeals process. I am certainly not an attorney, and reading the language of the ordinance can be confusing, but, since the ordinance applies to both Airbnb and VRBO, it may be worth revisiting the ordinance with your attorney, and see if there are specific sections that apply to you where you might have the basis for an appeal. Financial hardship, for example.