Itunes could not copy [File Name] because the file could not be read.

Im trying to sync my ipod with my newly updated collection in itunes. But im getting the above error on random songs during the update process. Sometimes it will get 100/3000 songs complete before i get the error. Other times it only gets 4/3000. There doesnt seem to be a connection to the songs it has trouble on either. Some of the songs are newly added, and some of the songs i already had on my ipod. But it seemed to want to wipe my ipod clean first because i had changed too much in itunes or something. After i get the error itunes seems to think i have disconnected the ipod and wont detect it again until i unmount/mount again. My ipod library also stays empty, even when it gets 100/3000 songs synced before the error.
I am using windows 7 and an ipod touch version 4.2.1

Two possibilities come to mind.
Check your source hard drive for errors, right-click on the drive holding the library, click Properties, tools, check for errors, scan for and attempt recovery of bad sectors...
Or...
Repair Security Permissions
Right-click on your main iTunes folder and click Properties, then go to the Security tab and click Advanced. If necessary grant your account and SYSTEM full control of this folder, subfolders and files, then tick the option to replace permissions on child objects which will repair permissions throughout the library. This is the XP dialog but Windows 7 shouldn't be too different.
If it won't let you change the permissions use the Owner tab to take ownership from an account with administrator privileges.
tt2

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