Hi amberbamber,
Welcome to Laptop GPS World. :welcome:
Unfortunately Microsoft Pocket Streets was never able to route from A to B. The product was a simple map viewer, and it was discontinued a couple of years ago.
For your amusement you may read Microsoft Knowledge Base article 319242,
MapPoint or Streets and trips exports the map but not the route information when you try to export a route to a Pocket PC. The article suggests that you save the map as a web page, and then view it on your PPC. That might have been a practical suggestion when it was originally written (years ago ), but it is a bit funny today.