I use MSC mode with Winamp to sync my playlists to the Clip. Works really well except for one gotcha. The Clip expects paths in the playlists to be relative to the location of the playlist instead of full paths from the root of the player. Winamp always puts full paths in the playlists.
I ended up having to create a little batch file to fix the paths in the playlists after syncing. I used the amusingly named FART (Find and Replace Tool): http://sourceforge.net/projects/fart-it/
. It's a free command line tool to replace or remove text in a text file. You might want to check it out.