Connect your iPod to your computer. Once the updates are all complete, choose a playlist from your iPod's list, not from your iTunes' list. Now do the following:
- Select the first song, then choose File: Get Info (or hit Command-I). In the new window that opens, go to the Options tab.
- Next to Start time, do nothing.
- Listen to the end of the song while watching the timer, and note the time that the music actually stops. Next to Stop time, enter that time. For example, the song 'Son of a Preacher Man' as sung by Dusty Springfield officially lasts 2:29:14. However, there is not much discernible sound at 2:23. Therefore, enter 2:23 where it says Stop Time.
- Go to the second song on your Playlist -- just click the Next button in the Get Info window.
- Next to Start time, change it from 0:00 to 0:01.
- Now repeat step three.
- Go to the next song and repeat the process.
- Continue until you get to the last song. Change the start time, but don't change the stop time. This will create a natural, rather than an abrupt, end to your playlist.
[robg adds: You'll need to have your iPod in manual mode to do this...]

