Depreciation is going to be worse on the more expensive models. As the initial purchaser you're effectively paying a premium to be at the 'cutting edge' that doesn't translate into an increased residual.

That said, pick up a $1,500 MacBook Pro and you shouldn't have any trouble selling it on for $1,000 after two years of ownership. Even better if you bought it with a student discount, and it has a three-year warranty (included with the student discount, at least in the UK).

It's something people often don't consider in the 'Mac vs. PC' debate. Yes, a MacBook Pro may be $200 more expensive than a similarly specced laptop from another manufacturer, but it's the total cost of ownership you should be considering, and PCs tend to depreciate an awful lot worse than Macs...