joe,
Musicmatch Jukebox is pretty good and amongs the folks I know, would be their preferred option, if they didn't own an iPod.
However, at least one of them uses Musicmatch for everything except putting tracks on the pod, because they feel the interface is much better.
I have recenlty just made the switch myself from iTunes to Musicmatch, although I now have a Sony MP3 20Gb hard disk player, which like the pod, requires its own software to get the music on-board.
Regards,
Shuttlebus