Our company writes routing software that can export a route into MapPoint. I then go into Route -> Route Planner and Optimize Stops. There's something I just can't figure out about route optimization. Sometimes MP sends the driver down one side of the street, has them make stops elsewhere, then has them come back to the first street to collect the other side. But sometimes it seems to make all stops on a given street sequential, so the driver is sometimes stopping on the left, sometimes on the right. We have clients who prefer different settings. Does anyone know a) why MP doesn't seem to behave consistently in this area and b) if there's a setting I'm missing somewhere to either make it ALWAYS stick to one side of the street or ALWAYS do all the stops on a street in order? Thanks.

There is no such setting... there are much more sophisticated route optimization software packages, but they are also much more expensive. e.g. TourSolver However if you are doing a lot of complicated routing it might be worth investigating!

If the areas you are dealing with all have say odd addresses on one side and even addresses on the other side, you could manage the waypoint order this way.

Hope this helps!

Eric