Hi! I have the same problem as you have with the 8GB nano. Even wiping it clean and re-syncing from the entire library, I found that I ended up with many of the same songs. To get around that, I created several playlists of around 7.5 GB, and you can even put the same songs in several playlists if there are songs that you really like. So, when I feel for a change, I re-sync it from a different playlist. On the Music tab, there will be a list of all your playlists, and you can select one or more playlists. If you select only one playlist, it will sync the iPod with only the songs from that playlist. That's the only way I found that will give me all "fresh" songs every time. I hope this helps!