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You'd better cleanup your iTunes library firstly. Just click "View > Show Duplicate Items" and then you would just check off the duplicates that you wanted to remove. After removed all the duplicates in your iTunes, sync it to your iPod, then all duplicates in your iPod will be removed automatically.
Source: http://how-to-delete-duplicates-in-itunes.newgenresoft.com/ How to Delete Duplicates in iTunes 12 11 10 9 automatically
To sync games automatically to iPod nano, connect your iPod to your computer. Then...
1) In iTunes, select iPod nano in the source list and click the Games tab. 2) Select “Sync games.” 3) Click “All games” or “Selected games.” If you click “Selected games,” also select the games you want to sync. 4) Click Apply.
Hey here is an apple article about your error 1439....
Last Modified: October 01, 2008
Old Article: 304508
SymptomsWhen restoring or updating an iPod in iTunes 7 or later, you may see a dialog reporting "An unknown error has occurred" followed by the error number 1415, 1417, 1418, 1428, 1429, 1430, 1436 or 1439. Products Affected
iTunes 7 for Mac, iTunes 7 for Windows, iPod nano, iPod shuffle, iPod mini, iPod, iTunes 8 for Windows, iTunes 8 for Mac
ResolutionIf you are experiencing these errors, begin by updating to the latest version of iTunes. When you have the current version of iTunes, try the following:
Disconnect and reconnect your iPod and then attempt to restore.
Restart your computer and then attempt to restore your iPod.
Disable or Enable Disk Use on your iPod and then attempt to restore.
Try connecting your iPod to a different USB port and then attempt to restore.
Remove any third-party USB devices you have connected to your computer (it is not necessary to remove your keyboard or mouse).
The 5 R's:
Reset, Retry, Restart, Reinstall, Restore
Remember these five basic suggestions if you have a problem with your iPod nano. If
one of the following doesn’t help, read on for solutions to specific problems.
â Reset your iPod nano. See “General Suggestions,” below.
â Retry with a different USB port if you cannot see iPod nano in iTunes.
â Restart your computer and make sure you have the latest software updates
â Reinstall iPod and iTunes software from the latest versions on the web.
â Restore your iPod nano. See “Updating and Restoring iPod Software” on page 50.