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If you consider future proofing to mean the best bang for your buck long term, then a slightly older refurbished model is often a way to go. ...Because the OP is even considering using the same computer for more than 5 years, I suspect the use case is pretty light, i.e. no intensive computational needs due to photo, video editing, game development or scientific number crunching.

Yeah, I think when most people say they want something future proof, it's really shorthand for asking how they can buy the best tech for the least amount of money. In those cases, just go refurbished or wait for a deal like the one B&H was just offering on 512GB 2017 Macbook Air models for $999. You'll end up saving more money and time going that route than by trying to time your purchases.

I don't think that we can say that anyone who wants a computer longer than 5 years is only needing it for light purposes though. I think that was true a decade ago, but less true once SSDs became affordable. I recently had to setup an old 2009 MBP to use temporarily as a backup machine for my Web development work. To my surprise, it was capable... not ideal, but workable in a pinch.

Personally, I delay upgrading as long as possible because my filesystem is complex and anytime I have to upgrade I lose many days of productivity.
 
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Current gen is actually pretty future proof because every time the keyboard breaks you get 1) new keyboard, 2) new trackpad, 3) new topcase, and 4) new battery under a recall warranty. Battery is the most disposable part and the keyboards break a lot, so you'll prob get a new battery every year or so.

The biggest technology to wait for though is 802.11ax. New wifi standards come around every 5-10 years and have the biggest real performance impact for most people.
 
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