The frist thing to do, I always say, is speak to staff and try to find out if they know why the regulation exists. If they don't know, keep going up the chain of command until you find someone who does. Speak to everyone you can, and if they still can't help you, get in touch with any elected officials you can find (city council, etc.).
By the way, when contacting City Council members, you can always save time (and ensure that your request is on the public record) by sending a group letter directly to the City Clerk, with a note requesting that the clerk forward the letter to the Council.
You may get nothing out of the whole process. Then again, you may just find a sympathetic ear that can champion your issue from inside the city.