Scrrem,
I had the same problems and it drove me crazy. I found a method of getting the routes into the unit that works fine, but I am sure that a better way exists. I did download the most recent updates and all, but that still didn't allow the Mapsource program to recognize my Zumo for transfer to operations. It will load existing data from the Zumo(waypoints etc.) to Mapsource, but ..... To get routes created in Mapsource into the Zumo, I did the following.
1. Create a simple route on your Zumo and then select to Share it. This will create the required folder structure for your route data on your SD card.
2. Create your route in Mapquest and then simply save it as type GPX (Garmin Exchange Format) to the GPX data folder which was created on your SD card either through your card reader on your computer or the supplied USB cable connection.
3. As soon as your Zumo resumes GPS operation (unplug the USB cable) or install the SD card with the newly saved data, it will prompt you that it has discovered shared routes and will ask if you would like to import them now. Press the Yes key and Viola! The newly created routes are in your Zumo for selection and riding enjoyment. Hope this helps. If I discover some other means to allow Mapquest to transfer directly, I will post it here.