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Well Brad...with mac now you have a choice using the newly released Boot Camp.
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Red Herring. Having Boot Camp is absolutely no good if what you want to do is sync iCal and Address Book, NOT Outlook. BootCamp is no help whatsoever. If he wanted to run Windows, he'd be running Windows.
I am, btw, typing this on my iMac. I have installed BootCamp and Windows XP, and I use it for some applications. But for my PIM functions, I use OS X, and for that I have a Palm Z22 and The Missing Sync.
I don't think most people care about choice of an OS. Most people just buy what they're told to, buy what they use at work, or go with what everyone else they know uses. What people want are applications that will do what they want. It's the apps that sell the OS, not the other way around.