I asked this awhile back and I'm not sure if there are any updates, but since MapPoint Web Services doesn't do route optimization, we've created our own. That said, a weak point is that we're using "As the crow flies" distances between coordinates for the distance part of our optimization. In practice this technique works okay 95% of the time but is problematic with tighter inner city routes which contain a lot of 1 way streets. I'm pretty sure that MapQuest has something called a distance-matrix that provides the user with a driving distance between each point and the others. For 10 stops this would be a 10x10 matrix which would be pretty expensive using existing MP transaction costs. Is there anything equivalent or somekind of clever technique using CalculateSimpleRoute that I could use to generate such a matrix.