I keep getting an error message when I try to sync

The error I am getting is:
iTunes could not sync calendars to the iPhone "Patricia's iPhone" because the sync server failed to sync the iPhone.
Now, this is where it gets weird - it is actually syncing my Calendar because new appointments are appearing in Outlook. The problem is that it will stop the sync so bookmarks, notes, apps, etc are not getting synced. I have a work around solution of removing the checkmark from Sync Calendar with Outlook in the iTunes program and then re-syncing but is there a way to resolve this so I won't have to sync twice?

My mistake in the additional info - it's Outlook 2007, not 2003

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