Well, it all 'sort of' works, the iPhone, MBP and PC sync OK.
However, there is a format discrepancy between Outlook and well anything really.
In Outlook, when you assign different diary entries a category (with an associated colour), iCal sees the calendar entries as belonging to just one calendar and therefore, doesn't split them into the different calendars.
Again with Outlook, if you assign contacts to different groups, Address Book sees these. However, if you generate a contact on the iPhone (or MBP) and assign it to a group, Outlook 'sometimes' reflects this. That said it does always appear in the search part of Outlook!
In summary, it does work, things do sync but not in the same formats (why would they).
Before starting I recommend adding one item at a time to the 'cloud' and backing up at every stage, just in case, as we did lose all calendar entries for a brief period
Hope this helps.