"Pros outweighing the cons" is often a solid indicator of a real Constitutional challenge, as most Constitutional protections are around things that the founder

"Pros outweighing the cons" is often a solid indicator of a real Constitutional challenge, as most Constitutional protections are around things that the founders decided had pros that outweighed their cons so substantially that they wrote them into the founding document of the nation. Your comment about illegal parking is a pretty good one for highlighting the consequences though - issuing tickets would become functionally impossible, which would likely result in more booting (which is effective at ensuring compliance by the owner, but wildly counterproductive to the goals of parking restrictions) or towing (which has plenty of its own issues). I've only started thinking about this today, so I don't have a strong opinion on this. I'm more interested in whether or not this sort of thing has every been seriously covered in court given its overlap with other privacy arguments.