I use a pc and have tryied iPod Access, Anapod Explorer, and iTunes and I think the "easiest" method of tagging the tracks is in iTunes, which isn't all that great. None of them do it fast. I make sure to give each track a name, artist, album and track number (you can do the album and artist all at once by highlighting all tracks and right-clicking to "INFO" or edit info I forget which.
Ex:
Artist : Lotus
Album : 2006-02-17 - The Fox Theater
Track 1: lotus2006-02-17t1
I didn't start doing it this way till last year and I'm working on cleaning everything up, very slowly...
http://www.timscales.net/ipod.htm