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Unfortunately iTunes doesn't let you transfer anything other than your iTunes store purchases from your iPod.
Totransfer all your iPod content, all your music, playlists, videos,podcasts and photos to your new iTunes library you will need todownload software like TouchCopy.
Here is how to use TouchCopy
Download and Install TouchCopy. Downloads are free and are available for both PC and Mac.
Start up TouchCopy by double-clicking the TouchCopy icon on your desktop
Connect your iPod or iPhone to your computer. TouchCopymay start iTunes - don't worry, TouchCopy has fixed it so that iTuneswill not sync music or video with your iPod while TouchCopy is running.These changes are restored when you quit TouchCopy.
Now select which songs you want to copy into iTunes, if you want toselect all your music, select "Music" from the list on the left andclick on "Copy to iTunes" button in the TouchCopy control bar. In a similar way, you can also use TouchCopy to copy your playlists, videos, podcasts, photos, contacts, calendars and notes.
Whenyou are satisfied that all your iPod content is safely in iTunes, useiTunes to re-sync your iPod which will enable you to add new content toit.
It let you restore it and you still get "unable to sync as playlist on ipod has changed"? I think that the restore was an erase and install and complete re-Sync of it. I think you need to try the restore function again and make sure it completely re-syncs before trying to do anything with it.
Does your ipod actually work or no? if it works put it in disk mode by pressing the menu and center buttons and holding until the apple appears and switching to the center and play buttons and holding until the check mark appears.
then plug it in the the usb and see what happens. if it mounts to itunes try and restore. if not go to my computer and see if it is there. if so right click on the drive and format...not quick format use full format. then repeat the steps before until you get it mounted. more than likely you have a virus and the virus is not letting the restore program delete it.
I'm not sure about error -48, but most often an error like this is caused by a corrupt music file not being able to be copied and stopping the sync. First, see if you can sync another playlist that doesn't contain any of the same songs. If it works, then it's just a matter of figuring out which song is corrupt. If you watch what song the sync is hanging on, sometimes you can pick it up quickly. ...good luck.
I don't believe its a File Problem, My lads Ipod has the same error -69 and will not sync, However it will also not sync on my Itunes which syncs fine with my 30gb IPOD and my Ipod also syncs fine on his computer.
So can't see where the file problem could be...
I know this doesn't help but there seems to be so many people looking in the wrong place (In my opinion)
THE SOLUTION IS EASY, REBOOT YOUR IPOD! IT WILL WORK!
I JUST SPENT DAYS GOING CRAZY ABOUT THIS!!! I CALLED APPLE TWICE AND THEY TOLD ME TO REINSTALL AND UPDATE BUT I DIDN'T DO ANYTHING..
THEN I FOUND SOMEONE WITH THE SAME PROBLEM AND ALL THEY DID WAS REBOOT THEY'RE IPOD.
HOLD DOWN THE MIDDLE AND MENU BUTTON ON YOUR IPOD, GIVE IT 10 SECONDS, LET IT BREATHE AND THEN PROCEED TO HOOK IT UP TO YOUR ITUNES(RESTART YOUR ITUNES AS WELL)...
VOILA IT SHOULD WORK AND SYNC...
Have you tried The Famous 5 Ipod R's?
1. Reset your iPod, iPod nano, iPod mini( http://docs.info.apple.com/article.html?artnum=61705 ), or iPod shuffle ( http://docs.info.apple.com/article.html?artnum=300595 ).
2. Retry your iPod with a different USB or FireWire port on your computer (please note that the latest iPods can only be synced through USB).
3. Restart your computer, and make sure that you have the latest software updates installed.
4. Reinstall your iPod and iTunes software. You can download the latest versions of iPod Updater (http://www.apple.com/ipod/download/ ) and iTunes (http://www.apple.com/itunes/download/ ) from our website.
5. Restore your iPod using the latest iPod Updater. Important: Please note that restoring (http://docs.info.apple.com/article.html?artnum=60983 ) an iPod will erase all songs and files on your iPod and restore it back to its original settings. Make a backup of any files on your iPod before restoring it. After restoring, you can transfer your music and files from your computer back to your iPod again.
Watch the Five Rs performance in action! (http://www.apple.com/support/ipod/tutorial/ip_gettingstarted_t16.html)
Did it help any?