I believe CoPilot has route optimisation which after inputting your 'destinations', or via's' it will sort from where you are to your final destination.
TomTom software has a route itinerary but you would have to enter your destinations/waypoints in the order in which you plan to visit. If you do the same pickups each day/week, you can save the itinerary to use another time.
When you enter your destination you will get an estimate of arrival time, which is fairly accurate under normal conditions. Once you commence your journey the ETA changes according to your speed and distance remaining.
TomTom ONE from >
http://www.globalpositioningsystems....15-in-car.html at £254.95 is well within your budget.
Whichever unit you decide on, make sure you have full postcode search for when there is no house number, only a name, or you are calling on a block of flats.