Syncing Issues between Ipad 2 and MacBook Pro

When we sync our ipad with our macbook pro we get over 100 errors for songs that won't sync to the ipad.  These are all songs we have purchased on itunes or downloaded from cd's.  Anyone encounter this before and have a suggestion on how to fix this?
Thanks

The underlying issue here is that you have chosen to use POP3 rather than IMAP mail accounts. Only IMAP mailboxes are 'synchronized' by default: it is virtually impossible to synchronize POP3 mailbox content.
For a discussion of POP3, IMAP and mail synchronization options, take a look at the Mail & Address Book - Tiger forum located here.

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    Read this whole message before doing anything.
    Back up all data.
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