Syncing Playlists with Windows Media Player

@jeffm wrote:

…it seems that you also have to create separate folders for each playlist.  Also, each folder has to contain all of the music for that playlist.

The latter is a very misleading advice and actually completely wrong. You can create playlists with Foobar2000 or Winamp (and others) and save them on the Sport. It’s simple: Connect the Sport to the computer, open the Sport’s drive, open Foobar, drag and drop the folders or files from the Sport you want to add to the playlist to Foobar’s playlist editor, choose «File» / «Save playlist…» and save it as .m3u to the root folder (!) of the Sport.