Having recently bought a clip+ I began experimenting with playlists. My initial attempts with lists generated by mediamonkey failed. The player saw the list but declared it empty. On another post I saw the first line had to be #EXTM3U and I put that in but that didn’t work either. The solution is actually stupid easy. Any app that creates m3u playlists will do. I’ve seen instructions for using wmp but personally I find it clunky and awkward so I shy away from it. I’ve used mediamonkey and vlc to date and both are fine although in mediamonkey you have to put that #EXTM3U line first. The trick is placement and for me what works is the root directory of the player or its extension. Then load the playlist in a text editor and remove the leading drive letter, colon and backslash from each line. That’s all there is to it. Once the player refreshes itself your playlists will work fine.
One thing I neglected to mention: the player expects dos format filenames so if you use vlc under linux or any other playlist creator in any os other than windows replace the forward slashes with backward ones.
May I suggest that you click on the Options in the upper right-hand corner of the message and edit your Subject line?
Simply “playlists” doesn’t tell anyone looking that there may be help or a solution to a problem they’re struggling with inside so they may not click on it. They just may assume it’s yet another of the hundreds of questions about playlists one can find here.
Something like “Playlist Solution” or “Problem Playlist? This May Help” might be more appropriate. 
