For some reason, especially videos I have are uploading on every sync I do. I notice that the video files are in the right place on the Zen and show up on the list, but the metadata I have in MC11 for Artist and Name go missing when it reaches the Zen. As a result, I believe MC11 thinks the files are not already there and re-uploads them, causing duplicate entries. I just tried a third time and it wants to upload them again...
When I look at the file paths on the Zen, I see the same exact path listed down to the filename, I am not sure how this can physically happen, but maybe the zen can distinguish the files internally. Anyway here is a screen cap of what I am seeing in MC11.1.188
For the Zen that seems to dump some of the metadata on transfer, it would probably work better if rather than comparing the metatags, MC11 would compare the file names on the device vs. the file names that could be queued for sync.
Any assistance would be appreciated...