Why do some songs in a playlist not play, or stop after only 1 song?

I've had several playlists on my ipod that stop after playing 1 song/track, as well as skip over severl songs in that playlist. I know the tracks are good, because I can play them in iTunes, as well as play them one by one manually in the playlist.
I've restored my ipod to factory settings, then re-synced everything, and i still have this problem.
I thought the HD may have some bad sectors, so I tried running the Hard Drive scan, but that option does not show up on the I/O menu when I am in diagnostic mode. (I have a separate UNANSWERED post about this too)
Message was edited by: Tony Cappellini

You could try a format of the iPod in Windows. A full format does a check and remap of bad sectors on the iPod hard drive, and you would need to restore the iPod as normal (using the iPod updater) afterward. This can also work when the iPod is recognized by the computer, but not by the updater.
First, put the iPod into forced disk mode.
See: How to put the iPod into disk mode.
On your PC, go "my computer" and right click on the iPod, then choose "format". Ensure the settings are at "default" and that "quick format" is not checked. Now select "format". It will take a while, but when that's finished, restore the iPod using the updater.
To exit forced disk mode, reset the iPod.
How to reset the iPod.
You can also check the iPod's hard drive for errors using Windows ScanDisk.
Put the iPod into disk mode as previously mentioned. Go to "my computer" and right click on the iPod then select "properties", then "tools". Select the option to scan the disk for any errors.

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