another vote for winamp here - i swear by it.
although saying that, there is an application called
floola which is fantastic.
it's very visual and allows you to drag and drop your songs onto your ipod and manage your playlists e.t.c..
the editing is top notch as well - you can edit multiple items, upload album cover art and do all sorts.
the one and only downside is that it doesn't seem to work with the latest version of the ipod software.
i know when i last tried it, it loaded and ran ok, but when i tried editing a song, it crashed and wiped the itunes database on the ipod so it showed up as zero songs.
the author just doesn't seem to have been able to get around this problem sadly otherwise i'd use it instead of winamp.