syncing with an external drive

I bought my Dad a Sansa Clip and he doesn’t want to store any files on his PC, but rather an an external flash drive, and then use the flash drive to sync the Clip through Windows Media Player.  We tried to do this, but Windows Media Player would not sync the files, they all came up as in error.  The computer and Windows Media Player see both the Clip and the flash drive where all the music files are, but it still won’t sync.  I would just tell him to drag and drop files, but he also wanted to create a playlist and the player does not see to read a playlist file that I dragged onto the Clip.  What I want to know is, is there a way to sync music to the Clip from an external flash drive using Windows Media Player, or a similar program that lets you create playlists?  Thanks.

try searching this forum for .m3u playlist. pretty sure m3u playlists work with drag and drop.