There are not two men sitting in the Jeep that pulls up. Just one, and once he has the car parked, he slides over and gets out the passenger door. I think the guy feeding the parking meter has scoped out the cars near the meter, so is in cahoots with the Jeep driver/thief. Meter man told the other that there was a large purse/bag in the front seat of the car that was broken in to.
That could be. I was wondering the mechanism myself, you might be right. Someone might well be walking up and down the street looking at cars, that kind of thing.