It's established that when Jack and young Stan were using the garbage truck, Jack secretly smuggled things around without Stan's knowledge, which now Steve accidentally gets involved in. However, the way it works is that while the driver is not involved, the garbage handler uses compartments in the back for the smuggling while handling the garbage. And Stan says "The Big Man operates the lever, the Small Man handles the garbage". Stan is now doing Jack's old job, Steve is now doing Stan's old job, Stan would have had to know about the smuggling back then.
The bus stop sign faces the sidewalk, away from the street. However, it should face oncoming drivers on the street thus informing them about bus stop restrictions (e.g. no parking).