Yes - always sync playlists, not folders of songs. Everything just seems to work better that way. I use Sony's Media Go on windows to load up my library, then c

Yes - always sync playlists, not folders of songs. Everything just seems to work better that way. I use Sony's Media Go on windows to load up my library, then create playlists from albums I want to play, then sync the playlist to the device. The app is smart enough to not upload a song twice if it is in 2 different playlists, and will not remove a song until all playlists it belongs too are removed. Media Go also has fairly good TrackID integration, so let it download album metadata before syncing to your device.