Mini stops syncing after just over 100 songs

My mini was working fine but I noticed that a couple of songs I usually listen to skipped in the same spot and one even began to lock up my ipod. I hooked up my ipod to resync all of my tunes. I have about 750 songs on my ipod normally, but after about 70 songs had been uploaded it really began to slow down and at 110 or so it stopped syncing. It says it is uploading but there is no progression. I then cannot eject my ipod and I have to force quit itunes. I've reset my ipod numerous times as well as tried to restore many times as well. Nothing seems to work. I still get the same problem every time I try to upload songs. Any ideas?
MacBook Pro Mac OS X (10.4.8)

I think maybe you should call Apple or contact customer service..You could probably update back to I tunes 6 because thats what I have right now on my computer and it works just fine with it..go to oldversion.com and you could try to reinstall 6..The last time I checked Itunes was unavailable. Hope this helps

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http://support.apple.com/kb/ht2519

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Matt,
I agree it was not all communicated real well, but in your case it will work out. You missed the program where you could have upgraded 100 tracks for 30 cents each (=$30) but now you can do it via Match (=$25). It works pretty simply, per this document:
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You need to delete the original DRM song from your library first. Doing this enables you to download the song again in the iTunes Plus format from iTunes in the Cloud.
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Click Music.
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Click the iCloud Download icon next to the song you want to upgrade.
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Thanks for the suggestion, and apologies for the delayed response.
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Mini stops syncing after just over 100 songs

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