I have Clip+ with the 16 gbyte SDHC. I use Windows Explorer to drag my folders and subfolders of .mp3 files from the PC into the music folder. Then, holding the Ctrl key down, I can select some of them, right-click, and choose " Create Playlist" from the popup menu. That choice appears when Settings > System settings > USB mode is set to auto-detect , which is the initial setting of a new device. It creates a .pla file in the folder I have open with the name “New Playlist”, which has to be renamed and dragged into the Playlists folder. That process works well for me, because I am not trying to make a playlist of individual tracks selected from multiple folders.
I also experimented with Winamp , which is better for those who want to pick individual tracks from a variety of folders. The USB mode has to be set to MSC. At one point Winamp asked if I wanted to manage the Clip+ “as a Winamp device”. Assuming I had no choice, I said yes. But I discovered later that means the " Create Playlist" option gets replaced by the Enqueue in Winamp option. To get back to the mode I prefer, I did several things, which might not all be necessary. (1) Set the USB mode back to auto-detect. (2) Uninstall Winamp from the PC. (3) Format the Clip+, which only affects the internal memory, not the SDHC. It took some combination of those 3 things to prevent the Clip+ from stubbornly reverting to its “Winamp device” identity without giving me a choice.
I also experimented with Media Monkey, but was too chicken to mess with my firmware version. I created playlists of type .m3u in the MUSIC folder of the external memory, but when viewed in the Clip+, they were always empty, no matter where I moved them to.