By Dan Moren

July 31, 2016 1:09 PM PT

By Request: Upgrade path

Subscriber Nathan writes: How do you decide when to buy new/replacement tech? How do you decide which models/upgrades are worth/not worth paying for?

Ah, the dilemma of every tech nerd: what do you buy and when do you buy it?

Let me start with some caveats: As somone who writes about technology, I buy a lot more gadgets and upgrade more frequently than anybody probably needs to. In the same way that I take a flying leap into the pool of beta software, I generally upgrade my tech frequently because it helps to be able to write about things.

That said, my perspective on this has changed a bit over the years. Before my career in tech writing, it was all about budget and how long I could squeeze use out of my equipment. I had a history of being one of those people who bought Macs about two weeks before the new model came out. Then again, back then Macs were about the only thing I had to worry about. These days, there’s so much more technology that it can be a little overwhelming.

At Macworld, I had the advantage of usually having the company pay for my devices, since it was a necessity to do my job. That wasn’t always the case—sometimes I paid for part or all of a device—but it definitely freed me up to worry less about budgetary concerns, though it was more important to stay on the cutting edge and remain relevant.

In my freelance career, I’ve become a bit more circumspect. I still need to keep my devices current in order to write about them, but I have to balance that with tracking my own income, figuring out the tax implications of those purchases, and so on. I also end up looking for deals and discounts a lot more, such as sales and refurbished models.

So, all of that said, let’s break this down by devices, since each has their own use case and upgrade schedule.

Mac: I currently have three Macs: a mid-2011 21.5” iMac, a late-2012 Mac mini, and an early 2014 11” MacBook Air. As you can probably tell from that, my Macs are hardly the latest and greatest—not a Retina display among them, for example. In most cases, I haven’t felt terribly left behind; all of them work pretty well, and I’ve done some upgrades where possible to eke a little more performance out of them. Macs are big expenses, but they are also a more mature product line that’s not seeing radical improvements in each cycle; currently, all my Macs do what I need them to do. Could they do those tasks faster and more efficiently? Sure, but that’s hardly a quantum leap in functionality that’s leaving me behind.

However, that doesn’t mean there aren’t functionality gaps. My iMac is too old to support Handoff and attendant technologies, so I can’t, for example, take advantage of AirDrop or use the upcoming Apple Watch Auto Unlock feature. While that doesn’t mean I’ll immediately run out and buy a new iMac, it does mean that it will probably be the next in line for an upgrade. Eventually. (At five years old, I suspect that I can get at least a couple more years out of it yet.)

iPad: I tend not to upgrade my iPads that often, especially in the last couple years. That said, I’ve actually gotten a decent amount of mileage out of selling old devices via services like Gazelle and buying refurbed devices at a discount from Apple or elsewhere. Technology is advancing a little more rapidly in the tablet space than in the Mac space, but the improvements are still fairly modest from generation-to generation—an exemplar of the long-running theory that iPad sales have slowed because people simply don’t upgrade that much.

My current iPad is an Air 2, and while I have been tempted by elements of the Pro, the differences simply aren’t significant enough to push me towards upgrading. (I admit that I’ve become more intrigued in the Pencil of late, but I’m not going to pay a premium for a new iPad just for the privilege of spending more money.) The Air 2 is a great iPad, and I don’t find it lacking for features vis-a-vis the Pro. I’ll likely sit on upgrading that for another year or two, unless there’s some huge jump in this year’s model, which I’m not really expecting.

iPhone: Okay, so this is the big one. It’s Apple’s flagship device, and the one that generally sees not only the most meaningful technology improvements, but also gets the most attention from the tech press. I’ve owned all but one model of the iPhone—there’s a 5s loaner on the desk in front of me as I write this, but I never had my own—because I wrote a lot about iOS and the iPhone, and almost every year saw major feature additions that needed to be documented.

Last year I bought into the iPhone Upgrade Program to ensure that I would be able to trade in my phone every year and get a new model, but I’m actually on the fence about the rumored iPhone 7. It’ll end up depending if the advances therein are so significant that not upgrading will leave me out of the loop, and whether those hypothetical advances offset any potential downsides, such as, say, oh, not having a headphone jack.

Other: I’ve owned two Apple TVs, a second-generation model (which is still in use by my parents) and a fourth-generation. I skipped the third-gen since its changes were mostly pretty minor. It’ll probably be a while before I need to upgrade the set-top box again, given how infrequently Apple revs it.

The Apple Watch is too new at this point to have an idea of how often it will be refreshed, and how significant those changes will be. Only with watchOS 3 has the device seemed to approach its initial promise, so there would have to be some pretty major upgrades to convince me to buy in for another generation.

To buy or not to buy, that is the question

In the end, I tend to think that the calculus is pretty simple; I won’t even slice it between “need” and “want,” because even there it depends on your own personal restrictions. If you’ve got all the money and space to be able to afford all the latest and greatest gadgets, then have at! But if, like most of us, you’re constrained on those fronts, then it’s a matter of really thinking through whether the advances over your current setup are so great that they tilt you in favor of upgrading. (And, of course, I highly recommend passing along old tech to those who could use it, whether it be family, friends, donations, or even just selling it online.)

[Dan Moren is the East Coast Bureau Chief of Six Colors. You can find him on Mastodon at @dmoren@zeppelin.flights or reach him by email at dan@sixcolors.com. His latest novel, the supernatural detective story All Souls Lost, is out now.]