Well, after an hour on the phone with Apple (level 2 support), they basically admitted that they are aware of a problem with the iTunes sync plugin for Outlook. They have escalated the problem to engineering, and are hoping for resolution soon (whatever that means).
I have spent (wasted) about 5 hours trying everything I could find on the apple forums, here, and anywhere with only transient luck. After reinstalling iTunes and re-enabling the plugin manually in Outlook, I got the iPhone to sync contacts and calendar once. Since then, no syncing, and I still get the Outlook error every time it launches.
Let's hope they fix this soon.
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