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I agree about using Google contact sync. You can import all your Outlook contacts to Google and all your contacts will sync w/o even syncing to your pc.
Thats what I did. When I first got this phone I sync'd with Google and Outlook and had doubles and triples of some contacts. After dealing with this after a few hard resets I was motivated enough to export all my Outlook contacts and import them into Gmail, then go through them and delete any duplicates and assign them to groups. Now all I have to do is sync with Gmail and everythings groovy!
Ive ben syncing contacts with google for almost 6 months and havent had one issue what so ever, you might want to check and make sure the contacts in your gmail aren't duplicated because of outlook? Its just hard to believe google sync would ever mess up! there has to be a cause unrelated to google!