I've been playing around with this for the last few days and noticed that there is no way to sync Outlook with ical for iPhone/MobileMe syncing. It seems like the only way to get this is to use a MS Exchange Server instead to get cloud syncing of your calendars. I hope they release a fix as even Office 2008 Entourage used sync services to sync calendars.
Currently Outlook 2011 sync services only supports Address Book syncing.
I'm pretty sure this doesn't exist on the Windows side either. When our department moved to Google Calendar from the old Exchange/Outlook combo a year or so back, there was no Microsoft-approved way to migrate a user's data to any ical-standard calendaring system. Fortunately non-Microsoft tools exist
Given the dominance of the Exchange/Outlook combo in business, I'm not too surprised. If Google Calendar continues to grow, eventually Microsoft will come around because then it will make business sense - analogous to how Internet Explorer is now moving towards standards support.