I don't know if this is even the slightest bit relevant, but I use a free program called CopyTrans Manager. I build my playlists by creating a directory on my computer, file by file or even directory by directory, then use CopyTrans drag the whole thing into my iPod Shuffle. No Apple software of any kind required.

[Thank you, Tony, for steering me to CopyTrans about 10 years ago!]

tanstaafl.