I thought I knew just about all there was to be known about the iPod and the syncing of same, but — proving the adage regarding aged canines and new skills — forum visitor madmaxmedia set me straight ...

When you boot up a new Mac for the first time, Apple gives you the opportunity to copy existing settings, applications, and entire user accounts—including all data—from an existing Mac to the new one.

Simply remove that song from your synced playlist and sync again. If you do not want to completely delete the song from your iTunes Library, but would like your iPod to sync properly, try unchecking ...