Well i do have the same problem maybe a little different one.
I have checked all below on sync settings
Delete tracks that are not on the auto-sync list from the device
confirm deletion
or delete all tracks from the device and fill with random tracks
But when i start syncing it just tried to delete 3-5 songs from my device.Then tried to copy some random songs (from the selected playlists) and all gave me Copy Failed.
It doesnt always give copy failed but whenever i choose those options,it only deletes a couple,then copies eveything which makes device full of songs.Each sync with those settings makes the song count on device almsot double because it does not really deletes songs as it should before copying.
