Unfortunately after a recent hard-drive crash, I ran into a problem restoring our iTunes library. The music was fine and restored without issue, but the backup of the system files (that control the playlists, ratings, etc…) was corrupted on the backup volume. I spent a few days trying to piece things back together but to no avail.
Meaghan and I have since been putting our playlists back together by inspecting the contents of the lists on our iPods and arranging the corresponding songs accordingly; something of a painstaking process to say the least. Fortunately this morning I was able to get enough restored to reach a tipping point where the remaining playlists were better off being re-built than recreated. They were in need of a refresher anyway. Now I’m finally able to sync my iPod again and take advantage of the new music we’ve purchased in the last month. The ratings (1 to 5 stars) are still gone but I’m not too worried about that.