Shipment processing can be time-consuming and inefficient, but a custom module might considerably improve things, up to 60-fold even (from 15 minutes to just 15 seconds per order shipping). You can read more about how here 

this one might require custom module in order to answer your needs.

start with drawing all things on paper.

set your flows. (include returns)

create the list of trucks, drives

create the list of wares

create work orders / pickups / delivery orders

use bar-code on packages generated from that (to identify the vehicle, driver)

each terminal with identifier to keep track of the package (user / ware ? )

that's all comes out for now, it was long time ago I designed something like this.