Some time ago I was having the worst time getting my Contacts and Calendar to sync with iTunes. iTunes would recognize my iPhone and back it up as it usually does first thing. Then it would always get stuck on “Syncing Chace’s Contacts”. If I uncheck the contacts to skip that step it would hang on “Syncing Chace’s Calendar”.

I tried multiple fixes, including exporting all contacts, calendars from Outlook and closing, then re-importing them. I restored my phone both by clearing it completely and using a backup to restore and just by restoring without clearing.

Finally I tried the suggestions from the following post:
http://discussions.apple.com/thread.jspa?messageID=7671182

Along with the suggestions in that post and uninstalling iTunes, Safari, Quicktime and any other software from Apple, then installing a fresh copy of iTunes 8 I was finally able to sync my phone again. I am not sure what happened exactly but hopefully this information will come in handy for someone else!