ITunes 11 crashes on my Mac when trying to sync music to my iPhone

I have an iPhone 4 8GB and a fairly recent model of Mac (purchased this desktop in summer of 2011), and when I try to sync my music to it my itunes crashes. What's the deal?
-I have tried resetting both the computer and the phone.
-I have restored to factory settings.
-I have both of the most recent software updates for both the iPhone and the iTunes/computer.
I don't know what else to do..

Hi revsally,
Please see What userid & password do I need to install Flash Player?
Maria

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I recently installed an x64 version of Windows 7 Ultimate. I have an Ipod Classic 160gb (late 2009), and i am trying to sync it to my itunes library. However, everytime i do so, it will copy across a few songs (a different number everytime, no more than 500 though) my Itunes freezes up (as well as the ipod). After a while, once it "comes back to life" i get either "Itunes cannot copy {Song Name} to {Ipod Name} Ipod. An unknown Error Occurred (-50)." or "Itunes cannot copy {Song Name} to {Ipod Name} Ipod. An unknown Error Occurred (-69)".
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Enable Disc Use - No Luck
Uninstall / Reinstall Itunes + Rebuild of Library - No Luck
Uninstall Itunes, reinstall + Rebuild Library on Previous version (9.2) of Itunes - No Luck
Kill APSDaemon.exe While synching - No Luck
KIll all other Apple Services + Processes - No Luck
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You seem to have tried everything, and you say it's syncing fine on your Dad's iMac, so I assume, you have also done a Disk Diagnostic from an earlier post by tt2 and conclude that your iPod Hardisk is good.
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