I’ve tried of songbird however as IHN says it is a bit lacking and has a truely shocking memory issue as it doesn’t handle tracks in the same way as most media players.
In my opinion Winamp has the best playlist editor out there, fairly sure that there must be an ipod plugin for it out there too.
Also if you’re on linux I’d try out jokosher, it’s pretty good but once again not sure about the ipod support!
Also – I don’t use Itunes…because I don’t like it. I’m not massively keen on the way the playlist etc… works, I also don’t need a media library as I just use explorer to select tracks then enqueue em in Winamp