Fishfuzz,

Yes you want to be using iTunes OR MediaMonkey for your music but not both. Perhaps others might have ways around this, but my experience is that they'll interfere with one another if used for the same content.

What you can do is export your iTunes playlists to .m3u files, which MM can then read (I'm assuming that this is possible natively or with some iTunes script).

-Rusty

I'm having troubles with playlists. If I have playlists that are created in iTunes, and then resync in MM, those playlists get blasted. Expected behavior?

As it stands now, I sync in MM, then have to return to iTunes and recreate the playlists on the iPod Classic.