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When there are some common, easy-to-fix scenarios that can cause seemingly anomalous behavior, it's more efficient to rule them out first before diving into the more arcane situations, especially when the support staff doesn't have a good grasp of the technical ability of the person on the other end. Have you previously reported these issues to Omni? It's a bit much to get indignant about slow progress on an issue you haven't bothered to report!

I wish I could share your conviction that being able to sync with your iPhone meant that the sync machinery is all working properly, but I've spent a dozen hours in the last day and a half working with MobileMe tech support tearing apart my 51 calendars and putting them back together again, and it hasn't exactly inspired confidence. I've never had any use for the OF iCal sync functionality, so all my data corruption was done by Apple software. I'd say there's a good chance that both Apple and Omni have some bugs yet to be squashed in this area.