We did somethng similar for an armored car company.
Each driver's pickups are scheduled creating a pickup schedule for each location ( eg Monday, Wednesday, Friday - Last Wednesday of the Month, Daily, etc)

Once a week or so, they download the schedule for a given driver to a handheld device that the drivers uses to schedule his pickups.

It's fairly straitforward app. There's a location table, a schedule table, and a driver table.