So all they'd need to do is compel the driver to chalk his own car?
The typical method along those lines is paying at a machine, getting a receipt, and posting the receipt visibly inside the windshield or the street side window, but, yes. This was about physical trespass for information without sufficient cause, not a right not to have parking time tracked.
My experience though is this particular style of parking pass is usually on private property where the people checking are not part of a branch of police though, and thus I think are not bound against unreasonable search in the same way?
For example, I saw an article a few years ago where a cop was literally walking a drug dog around a house. The dog detected drugs so they busted the door down. The courts threw the case out, there was no reason for a drug dog to be searching around his house.
I’d expect if you had a drugs or a dead body in plain view of a window then your expectation of privacy is gone.
No, by the plain view doctrine information gathered at least by normal human senses without a physical trespass is not a search.
> Like, a police officer dragging a street by looking in every window for pot or guns would presumably be indiscriminately searching without probably cause
No, they wouldn't, just like a police officer indiscriminately looking through your car window for violations of cellphone use while driving laws without any particular cause isn't.
Without the physical intrusion, I don't think this ruling would apply at all.
In another sense, no, because what the chalk does is establish that this car has not moved since the last time the officer went by. If you chalk the tire yourself, the officer cannot know when you did so.