Thanks redwing.
If I understand correctly, it's not a sync issue with your iPod but a discrepancy between your database file and music files.
Yes, I would agree with this.
I would run File> Rescan files command with both "remove dead links" and "re-scan files already in library" option ticked. Also, delete those files ending in mbl and dat with the same name as your iPod device under AppData folder just to make sure the old data files won't affect your syncing. BTW this kind of discrepancy will always happen if you delete tracks with MB closed.
I was really excited to read this. I had failed to mention initially that I had previously rescanned, but without the second option. Nor had I deleted the two MBL and DAT files. However, I don't see the iPod's MBL or DAT files in AppData. I do see them for my Android phone which I occasionally sync with just a few playlists. But my entire collection is on the iPod. And that's where I'm getting the 'sync failed' error. But I ran the rescan and then did a sync and the result is the same as before - sync failed. And MB is showing the manually deleted files as not copied.
Shouldn't MB create the MBL and DAT files if they don't exist? I wonder if the fact that they don't exist is (part of) the problem.
BTW, here's two lines from the error log, which confirms that for whatever reason, MB is looking to sync files that no longer exist.
6/10/2014 1:07:29 PM - Copy Z:\Derek And The Dominoes\Layla And Other Assorted Love Songs\13 - Layla.mp3: File not found
6/10/2014 1:07:29 PM - 6.1.7601.65536 - 2.4.5273.38538 - System.IO.FileNotFoundException: Unable to find the specified file.
Any other suggestions?
EDIT: Part of the mystery is solved. I found the MBL and DAT files in AppData. They're named with the serial number of the iPod instead of with the iPod's name. I deleted them and performed a sync with the same results as previously - sync failed.