I submit for your enjoyment, a story I heard about, and can vouch for it's authenticity:
I had my vehicle booted in downtown ATL some years ago. My full size SUV was too large for the hotel parking garage where my daughter had an event. I was referred across the street by the hotel staff to park in the lot they were "associated" with. (I later found out that associated consisted of they send people with large vehicles there). I had unknowingly bought the advertised $8 "overnight" parking pass (parking Saturday night at 10pm, leaving Sunday at 10am) instead of the "necessary" $9 "weekend" one). I called the office and spoke to someone who said they would have a manager call me back but in the meantime my only option was to pay the $75 fee if I wanted my vehicle back before Monday. (This has been summarized for clarity, it actually took me like 5 phone calls to get this information and to find out that no one was in fact calling me back before Monday).
I feel I handled it pretty calmly - having worked for a locksmith for ~10 years growing up it was somewhat trivial to remove the boot without doing any damage to it. I didn't want someone to steal his equipment though, so I asked the technician where he wanted me to put it (yes, he did pause for a second as we both acknowledge the easy joke we ignored). We had a discussion about the legality of the sticker he placed on the boot claiming it was a $500 fine for touching it (not just tampering - touching). I was somewhat annoyed and wrote on another sticker saying "don't boot my truck" and told him it was worth about as much as his sticker. He decided he couldn't accept the boot without having received payment to remove it - and didn't seem to understand my explanation that I didn't need his "removal service" - I just didn't want his property lying around in a parking lot. Finally I decided that by securing it to the tire of his vehicle it wouldn't be stolen - and I wouldn't be held responsible for the units (both of them, they put 2 boots on my truck). As an added bonus, I explained he could now perform his "removal service" and obtain payment for such.
He claimed he was calling the police, so I posed politely next to my vehicle for him to get a good photo (kill them with kindness right?). There are pictures of me somewhere - some of the local residents were cheering and snapping pictures as I left. I never got a call back from the company on Monday, and I never had any future contact regarding this issue so who knows!
In summary: an additional $1 could have saved me several hours and cost me a lot of amusement.
IANAL - my understanding is that you shouldn't interfere with boots owned by the city as they are public property and protected by law. In this case, it was a private parking company working for the owner of the private parking lot.