I went for a Google solution for my contacts because it's based on push technology so the phone & Outlook will sync every hour (user variable) without human intervention. (Google don't provide sync for contacts or I'd have sorted both data sets via Google).
- Download & install to your PC 'Google Calendar Sync' from here
- Tell iTunes to stop syncing Calendar
- Sign up for a free Google (Gmail) account if you haven't got one already
- Sync your info from Outlook with a One Way sync to Google
- Set up iPhone sync by following instructions at here
- CHECK EVERYTHING IS OK - particularly check that you haven't got a zillion duplicate entries before switching syncs to Two Way.
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