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The software needed will use a USB scanner to scan packages (PDF417) and enter the information into a DB hosted on a server. The software must account for multiple users scanning their own lists daily. Once a user has finished scanning the software must organize the route for the driver - or utilize something like Google Maps and add points.
This is the most simplest form of the software - features like using Fedex's API to receive delivery notifications would be eventually required.
Java/C++ for PC software to handle scanning and sending information to server. (PHP/MySQL)
Languages/Specific methods or technologies are open and not strict and can be discussed.