I think it's pretty clever.
He probably pays some kid to go around looking for expired parking meters, pay the meter and leave a flyer. The kid's keeping out of trouble and happy for some pocket money. The car owner is protected from a ticket. The only unhappy people is parking enforcement. The local government will probably find some arcane law to keep the insurance salesman from doing this.
Reminds me of something my parents use to say "No one has endurance, like the man who sells insurance".