When I was first starting out, I was sent to a rental property to clean it up after the tenant passed away. The landlord applied to the city to have a handicapped parking space created for the tenant on the street in front of the house. I thought it would be okay for me to park there after I saw the neighbors parking there with parking enforcement passing by and none of the neighbors got ticketed.
After a while, I tried parking there and got ticketed immediately. I fought the violation on the grounds that the space was originally a public parking space, requested by the property owner for a specific tenant that is no longer living and I was there at the owner's permission and request.
I went into court where naturally, I was found guilty, as expected, because they haven't heard the backstory, but I filed for an appeal going in. I had to go through the back and forth process with parking enforcement to actually get a court date to sit down with a city official in parking enforcement. The official started off by asking me very bluntly "Do I think that I can just do whatever I want with no respect for the law?" I am going to assume he assumed I was not there for a business purpose, and he also was not aware the tenant using the space was no longer living. Keeping my composure, I explained I had never done that before, I was aware of the purpose of the space, but that the space was alloted to that specific property and a specific tenant for a specific purpose, the tenant the space was allotted to was no longer living, the property was vacant. I argued the concept of licensing in the real estate sense. The owner of the property requested a license to accomodate a tenant.
I was there at the request of the owner to do cleaning and light repair work, otherwise I wouldn't have been at the property. With the tenant's passing the purpose of the license no longer existed, so logically I shouldn't be held liable for a license that no longer had a function. Yes, I understand this is a "handicapped" curb, however, it's also literally just a blue spot on the curb now. And also, the law was being enforced arbitraily. If anyone would have a complaint, it should be coming from the owner, but the owner had no problem with my action, so how can the city arbitrarily choose to enforce a rule if the party that would have a problem with me clearly stated they don't have a problem? By the way, as a teaching moment, when in court settings, I have had to be prepared on other occasions to defend against the judge or adjudicator seeing an offense where the party that would be offended stated they had no issue.
The official took roughly a month, and with my documents (statement from the owner, picture of the orientation of the space, picture of parking enforcement passing by while another car was parked in the space without receiving a ticket), he found in my favor and decided to overturn the violation.
One of my fears in the modern world as things change and technology grows is that we are slowly losing the ability when dealing with corporations and government to be able to sit down with someone that actually has power to change anything. As a side note, I observed something similar that might have helped lead up to the subprime crash in the '00's. From my experience, before the crash, when you called a lender as an investor, there was someone you coould talk to on the phone that you could negotiate with, as long as your position was solid and you maybe just needed a tweak to the terms or a break. The lender would also consider things like if you had equity in the property, other property as collateral, or if you had a past record of following through and delivering if they made a concession for you. Just before the crash, calling a lender became like calling on a credit card or car note lender. You shuffled through the phone mail system, if/when you could get someone, the people that answered the phone needed a lot of uneccesary information before they could even pull up your account, and then they couldn't do anything outside of offering basic information or collecting a payment. And it became almost impossible to reach someone who had real estate knowledge, when prior to the crash it was standard for whoever answered the phone.
When confronted with a complex situation that has multiple layers, keep calm and unpack the layers of the situation in a logical manner in order to get your point across, and sometimes they other side may be willing to change their position or decision without conflict.