IPod and iTunes freezes while uploading music

So a couple of weeks ago, I was using my 40Gb iPod when suddenly it froze. I reset it but when I tried to play another song, it skipped all of them as if they weren't there. I had lost my entire library in an instant. Once I got back to my computer (Powerbook) I managed to restore it. During this the folder with the exclamation mark and the run-click-run-click problems showed up. Now after successfully restoring it, I can't get my music back on it. For some reason at various points in uploading songs (whether it be after 20 songs or 2000) both my iTunes and iPod freezes. I normally reset it which causes the "improper device removal" sign to come up. Then when I plug it back into my computer I get the message that iTunes can't recognize the information on my iPod and that I need to restore it again. However sometimes it takes 3 or 4 times of it freezing during uploading to get that message. Either way, I can't get my library of music back onto my iPod without it freezing. I never see the folder with exclamation mark and the music that I do managed to get on there works perfectly fine.
Does anyone have a clue what is wrong with my iPod and is there anyway to fix it?

I tried the update with no success. Here's another update after actually trying to use my iPod:
When I have it just plugged into headphones or speakers half of the songs cut off in the middle, just a little bit off near the end. Some don't work at all. Plus my iPod is very slow while moving through the menus.
When I have it plugged into the Monster FM transmitter, I really can't get anything to work. It freezes on almost every song. The most I can get a song to play is about 16 seconds before it skips over to the next.
This seems just seems really messed up but it seems to be a software problem. Any ideas?

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Message was edited by: 4tna
Message was edited by: 4tna

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Place the iOS device in Recovery Mode and then connect to your computer and restore via iTunes. The iPod will be erased.
iOS: Wrong passcode results in red disabled screen
If recovery mode does not work try DFU mode.
How to put iPod touch / iPhone into DFU mode « Karthik's scribblings
For how to restore:
iTunes: Restoring iOS software
To restore from backup see:
iOS: How to back up
If you restore from iCloud backup the apps will be automatically downloaded. If you restore from iTunes backup the apps and music have to be in the iTunes library since synced media like apps and music are not included in the backup of the iOS device that iTunes makes.
You can redownload iTunes purchases by:
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Back up all data.
Triple-click anywhere in the line below on this page to select it:
~/Library/Application Support/SyncServices
Right-click or control-click the line and select
Services ▹ Reveal in Finder (or just Reveal)
from the contextual menu.* A folder should open with an item selected. Quit the application if it's running. Move the selected item to the Trash. Relaunch the application and test.
*If you don't see the contextual menu item, copy the selected text to the Clipboard by pressing the key combination command-C. In the Finder, select
Go ▹ Go to Folder...
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plug in my ipod and itunes freezes instantly, give it a few minutes and it slowly starts working untill it says cant load files, now can we not put m4a onto ipods? and if not why on earth did itunes decide to put it on as that?
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Antivirus has a tendency to freeze iTunes sync Operation with iPod Classic, causing a timeout, which corrupt your iPod filesystem, so when iTunes can't read the iPod, it is pointing to this problem. Other causes is when your iPod hardisk is dying, or your battery is dying causing hardisk crashes.
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Connect your iPod to the PC and run chkdsk, to fix any iPod diskerror, then disconnect it, after chkdsk complete.
Disconnect your PC from Internet. (just to make sure no nasties creep into your system while you syncing.
Stop the Antivirus program
Connect your Ipod to the PC
When iTunes Open up, Restore your iPod please, this is for iTunes to map correctly, to fix the corrupted filesystem.
When Restore complete, eject the iPod and reconnect again.
Sync your ipod, preferably manually Manage in small batches and disconnect after every batch, to check that all is well, since you got such a huge library.
When all sync is complete, and iPod disconnected, start back your Antivirus and connect back the Internet.
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ITunes Freezes While Syncing iPod!

Hello,
I've seen tons of unanswered "itunes freezes" posts, but I'm hoping to get lucky. Before I even upgraded iTunes, a freezing problem started happening.
Anytime I copy some mp3's to my ipod, I see it add them all and then it goes into the "Syncing iPod - Please Wait" message, and iTunes freezes every single time. In order to use iTunes again, I have to completely CtrlAltDel and close iTunes then disconnect and reconnect my iPod. After I'll be able to reopen iTunes and use it until I have to sync my iPod again.
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Message was edited by: livingaftermidnight

OK, I read your first message again and can't seem to see where you wrote you didn't have all the music on your PC, but never mind, at least we got that straight before you went and restored your iPod!
I'm afraid you've run into the situation where it is risky to only have a copy of your music on the ipod, because everyone needs to restore their ipod sooner or later....that being said, you can get a 3rd-party utility to copy your music off your ipod onto an external hard drive, perhaps?
Or else try an ipod reset (which will NOT erase the music on your iPod), but I don't think that is going to help your syncing woes.

IPod and iTunes freezes while uploading music

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