As a former pizza delivery guy (glad to see CT is actually featured in this) with a casual interest in supply chain and complex systems, this made my day. It makes me wish the place I worked at in high school had the means to equip the delivery guys with GPS tracking.
At one point in time (during a college summer break), I worked with my boss to optimize our delivery routing system. Our goal was to cut down on the total number of trips out the door by logically combining deliveries based on distance, location, and the current backlog of orders. If, for instance, it was a busy Friday night and we were (as usual) shorthanded in drivers, we'd get more aggressive in how many deliveries one driver would take at a time. If, however, things were a bit slower, we'd focus more on getting each order to the customer more quickly be doing more direct deliveries. So long as the customers were aware how busy we were (not always the case since our co-workers who answered the phones sometimes didn't operate in the same reality as the drivers), there were usually few complaints about timeliness. The big thing was training and communication. I even wrote a manual and gave it to my boss.
Then again, drivers had their own incentives. Most drivers were less willing to take two orders if their likely tip from additional orders was smaller than the order that was ready to leave the door (typically we'd have drivers wait a few minutes for additional orders going in the same direction). It took some convincing - I often said "We're in this together - I'll find you a big order for later."
But the strangest part about the pizza delivery business is how petty customers can be, especially those who have food delivered on busy nights. Look at all the work being done on your behalf. A ready-to-eat product arrives at your door on a busy Friday night, and you complain about it taking 5 minutes longer than the person on the phone promised and blame the driver. People: please. Go easy on the pizza delivery guy.