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Started on the 3GS.
Then upgraded to the 4 (1 year)
Then upgraded to the 5 (2 years)
Then upgraded to the 6s (3 years)
Still using the 6s today (4 years and counting) with a planned upgrade to the 11.

You can see the pattern. :)
 
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In my case, I updated for the iPhone 6 to the 11 pro. My plan is to keep the phone til the latest software is no longer available. Plus I tend to replace the battery like an old G.

Every year since the minute the first one released on launch day. The launch day delivery is a yearly ritual.
For me, either the previous phone is severely damaged or the performance is no longer tolerable. My target is to replace a phone every 3-5 years, aiming for 10 years when possible.
Ten years is a bit ridiculous - that's the difference between the X and the original iPhone which was basically unusable in 2017.
 
For me, either the previous phone is severely damaged or the performance is no longer tolerable. My target is to replace a phone every 3-5 years, aiming for 10 years when possible.
3 - 5 years is easy nowadays, but longer than that? The problem is that lithium batteries, even under ideal condition, won’t last that long. So unless Apple provides battery replacements for iPhones indefinitely, you would probably be looking for an upgrade by year 5 or 6.
 
Currently have an iPhone SE.

If it becomes unsupported in iOS 14, I'll probably take the jump and get the latest and greatest, whatever that might be. But I really wish they'd make smaller phones. The current line up is just way to big.

The size of the current iPhones is basically an mini iPad mini.
 
Usually 1 or 2 years, but last year I ran an SE and an XR but sold the latter as it was just a touch too big for me. This year I sold the SE as all and bought an 11Pro 5.8” and I’m loving it so far.

But if the rumoured smaller device is actually launched next year I will probably get that, as long as the specs are still decent.
 
One year and already after 6 months eager for new model. I love latest and greatest. Always going crazy at launch day and try to buy it first day possible.
I pay full retail price and sell “old” one year model in pristine condition (always in case and protective case from day one of use).
In that scenario I add about 30% extra money difference to new model (about 400 USD).
My buying habit is quite different than in USA There’s no  upgrade program
 
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Every year:
Original iPhone
iPhone 3G
iPhone 3GS
iPhone 4
iPhone 4s
iPhone 5
iPhone 5s
iPhone 6
iPhone 6s Plus
iPhone 7 Plus
iPhone X
iPhone XS Max
iPhone 11 Pro Max
 
I'm even stingier than OP.
I'll use a phone and keep it on the same OS it came with for the duration of my ownership (unless its something terrible like iOS 11). Then when it's been banned from the newest version of iOS, (iPhone 6 barred from iOS 13for example) I'll get another iPhone 2 generations ahead of my previous one. I have yet to ever buy the latest version of an iPhone. Prefer to stay a few generations behind.
I have my eyes on other toys. iPhone isn't the only toy in town
 
I bought a 5S new and kept it until 2 years ago when it shattered. Bought an SE to replace it and I'll probably keep it until it's trashed.
 
3 - 5 years is easy nowadays, but longer than that? The problem is that lithium batteries, even under ideal condition, won’t last that long. So unless Apple provides battery replacements for iPhones indefinitely, you would probably be looking for an upgrade by year 5 or 6.
Or I will just go for an out of warranty battery replacement to let it last even longer. Usually I will replace battery after two years because of the degradation.
 
I usually keep my phones for two years. I think that way you see a significant difference when you come to upgrade. I recently went from an iPhone 8 to the 11 Pro and the difference is night and day.

That's true 8 didn't has night mode only day mode. And 11 has both, sound decision!
 
In my case, I updated for the iPhone 6 to the 11 pro. My plan is to keep the phone til the latest software is no longer available. Plus I tend to replace the battery like an old G.

So far i was buying every year but this year's iPhone 11 series i am going to return it. It's getting heavier, ram is still the same (could have little satifaction if it was 6GB), feeling more expensive because my iPhone Xs Max 256GB is not fetching me good resale price. I will wait until the notch and all other issues are gone. Battery is amazing in iPhone 11 Pro Max, speed & screen. I don't use camera a lot and i don't have issue recharging the battery. Screens of the earlier iPhones are acceptable.
 
I've done 6S Plus .. 7Plus ... iPhone X .. 11 Max Pro .. thinking next move is when notch is gone ..
 
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