Upgrading from an iPhone XS.
In the past I’ve been on a 3yr cycle. In the future I think I will do 4-5 yrs. I have the 13 Pro Max. To upgrade I would need a massive improvement in the camera.
I have an XS Max. Two years ago I never had to worry about the battery and could make it through work without issue. (I spend alot of time outdoors at work). At 80% battery health I now have to keep an external battery with me to be sure I’ll make it to the end of a job. If anything gets me to upgrade, it will be this. The phone is still a joy to use otherwise.
I have a QI-Charger on my desk, so while working there, the Xs is just lying there and I have no trouble throughout the day with my 80% Battery.
And while I am away from home, I can charge the phone with a Holder in my car…
That’s a pretty good deal. That said, I can’t get Verizon’s best deal on service because I don’t have that many people in my immediate family - so they’d want a minimum of $65/month out of me.
So I pay $15/month to Mint instead and save quite a bit over Verizon. I guess I have to use that savings to pay for my phone. 
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“Not available in all jurisdictions”. I think that whole concept was a very US-centric one. I distinctly remember the displayed price for the iPhone 3G in NZ was full price.
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3G → 6 → 12
I might have to wait a decade for iPhone 24 to be released.
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I have more three years between upgrades. I went from iPhone → 4 → 6 Plus → XS → 13 Pro.
I’ll be waiting at least a couple of years before upgrading my 13 Pro, hopefully when a redesign comes along.
I know this from Germany (also Europe?), too.
Mee too, But I want the API so I can program some interesting things using it ASAP as well.
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Battery life issues ended my long term relationship with my XR earlier this year so I guess I now qualify as a member of the more-than-two-years upgrade cycle.
There seemed to be a point after XR launch that I realized that as far as iPhones and Apple Watches were concerned, yearly upgrades were no longer necessary for me.
I think I’ve settled on a Tick-Tock upgrade cycle of device upgrades: New iPhone one year and new Apple Watch the next. Personally speaking, I can’t justify upgrading both devices on a yearly basis.
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To go back to the original question – and it seems it is similar for other respondents above – I think it is absolutely a case of the devices becoming “good enough” at some point, making the regular upgrades unnecessary thereafter.
For me “good enough” was reached at:
iPhone 7
Watch 5
iPad Pro
Before those I was upgrading every year or two and the improvements were obvious and useful. Since then I have been upgrading as and when necessary – usually batteries or damage/loss.
The only exception for me has been the Airpods which continue to only live a short life by virtue of their batteries that cannot be replaced. I have to keep buying new ones every two years or so.
I was on a 2 year cycle up until the iPhone 7 when I switched to the Apple Upgrade program in anticipation of the X coming out the following year. I kept with yearly upgrades for the 7, X and XS. After the XS, I stopped seeing the point in yearly upgrades or even upgrades every two years because the XS did what I needed. I also preferred the size and color more than the more recent models. This year I’m finally upgrading to the 14 Pro but only because my phone is starting to show its age by overheating and lagging on iOS 16. I expect the 14 Pro will serve me for the next 3-4 years.
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If that’s the only reason, it’s worth waiting until the final release (and probably one update after that). The beta software contains tracking code that causes lag and overheating. I’ve just updated to the release candidate and my XR is running much more smoothly and battery drain is much reduced.
I’ve got an iPhone 7 which I love. It spent 3 hours submerged in my septic tank and when I finally fished it out, I learned it received emails and texts during its adventure. I hosed it off and it’s good as new. I’m only considering an upgrade because the latest iOS is unavailable and I would like a nicer camera. My family makes fun of me but I’m loyal to the devices that serve me well.
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I’m curious if other people have worked out the economics for selling here. I used to be on an annual upgrade cycle, thinking that selling a year old phone would get me the best price for it, and typically did pretty well on that front. But I think I went 8, XS, 12 Pro and now don’t feel a burning desire for the new phone. But I know that next year my 12 Pro won’t have much resale value. Better to sell now when it has value or save the money on the upgrade and just take a trade-in special from Apple or Verizon next year?
Rounding the numbers, here are Apple’s “up-to” trade-in rates:
iPhone XS Max - $210
iPhone 11 Pro Max - $370
iPhone 12 Pro Max - $530
iPhone 13 Pro Max - $720
iPhone 14 Pro Max cost (base) - $1100
So if history is any indicator, you lose $380 your first year, or $31/month. You lose $190 your second year, or $16/month. You lose another $160 your next year, or $13 per month. And then another $160 your next year, or $13 per month.
Unless the new phone has inherent value to you for some other reason, it would seem to me that your first-year loss is the most significant, and you go from losing $13-$16/month to losing $31/month by upgrading - so might as well wait until the upgrade is worth taking that hit.
If carriers are doing wacko incentive stuff based on their overpriced rates, that might affect that calculus. But in my case I’m using Mint Mobile, so I pay my low rate each month and have to get my own phone. 
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I have typically sold my phones on swappa, where the prices are significantly higher. The 12 pro max with 256 gb is selling for around $700 now (vs $530). The 13 pro max 256 is selling for around $900. There is obviously some risk involved there (as well as selling costs), but I’ve been ok so far.
Edit: and the 11 pro max 256 is only selling there for around $400, making it not worth the selling expense or effort vs the trade in value. So it does look like selling now is more valuable than next year, but maybe not economically worth it overall (in terms of incurring the expense of the new phone).
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I think I went: 4 --» 5 --» 6 --» 6S Plus --» 8 Plus --» 12 Pro.
The 4, 5 and 6 were pretty much picked up as soon as they were available. The 6S Plus was a gift and I held onto it for years. The shift from 8 to 12 Pro took place within a relatively short span (12 months?). The 8 is still a decent phone; I only picked up the 12 earlier this year for 5G and a camera upgrade, and I felt I could get away with it because they were both older phones at time of purchase and thus reasonably priced (I’ve opted to buy phones outright since the 6).
As long as iSmash continues to offer battery upgrades for less than £100, and unless there’s some particularly compelling new technology released in a future handset, I’ll most likely be using this 12 until it fails.
For phones I think I went from 3, 6, 6S, 8 and 13Pro (1TB) … I think I will stick to my 13 for a few years more, but I must say, the camera boost from 8 to 13pro was very much worth it!
As for watches, I am now on a Series 5, from a series 1 before that. I am waiting for glucose monitoring on the watch (series 10 or 11?)
For the iPad, on on 2018 iPadPro (iPad Pro 12.9-inch (3rd generation)) – will be a few years until I upgrade …
As for my Mac, currently on a MacBook Pro (16-inch, 2019), and hope to keep it for many more years … I may purchase an aditional mac mini with M2, when ever those come out!