I just downloaded the demo for S&T 2009. I like it and at the same don't like it. It could be an incredible program with a couple new/changed features:
1 - When calculating the distance/time, do it for the next stop, not just for the final destination. I add/remove locations as I go throughout my day. I can have stops added that I won't be at for a few days. I just want to see how far it is to the next stop, not until I'm done with the entire trip.
2 - Allow adding "waypoints" (not an actual stop). This would be to create a custom route if you need to bypass areas.
3 - Add a more touchscreen friendly interface, similar to iGuidance, CoPilot, etc.
4 - Allow the user to select POI categories that will pop-up and alert the driver as they approach them with a selectable distance, say 2,5,10,20 miles.
5 - Even though S&T has the ability to import pushpins, do them better. As a truck driver, I need different categories than just 1.