I've been forced to stare deep into the bowels of Apple's MobileMess, Outlook synchronization, and oddball .Mac conversion disasters.
This stuff is extremely hard, but Apple has brains and money. What in their culture caused such a massive screw-up?
The problem, I think, is secrecy -- an obsession with surprises that comes partly from their CEO (though if I read one more article claiming Jobs is Apple my brain will explode), partly from their history, and largely from an insanely successful marketing strategy.
The complexity of changing a densely interconnected system like .Mac to a very different system like MobileMe requires months of public beta before launch. There can't be any surprises, there has to be high reliability.
Google gets this. Microsoft gets this.
Apple won't be able to compete in the (cursed) Cloud if they can't kill their secrecy demon.