Considering Apple replaced my machine for free with a better one at the two year mark, I'm ahead of someone who takes the biggest depreciation hit and sells their machine every year. It might not cost a lot to upgrade every year, but it still costs more than someone who keeps their machine longer - it's no different than a car depreciation.
Actually, you're incorrect for the reasons I stated above. It's very different than car depreciation. There are a lot of people who vastly overpay for used models. I've actually made money upgrading a couple times—including my most recent flip. Like I said, you're making invalid assumptions.