Maybe I'm doing something wrong, but the deliveries in the bottom look to be correct. I've just went on a long joyride with the caravaner as he walked around Miller and gathered up supplies. Then walks halfway to Copper Hills, and turns around not delivering or picking anything up. He returns to Miller unloads everything, drops off cart, walks to center of town, and then goes picks up the cart, goes to gather everything again, and then repeats the process over and over again.
I thought with my setup he would go to Copper Hills, drop off and pick up, and return to Miller. Then get supplies for Tintown, go there drop off and pick up and return to Miller to start the process again.
I'm not sure if my setup is correct, but I'm pretty sure he should not be quiting halfway through like he is.