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I tend to wait until the leap in tech and designs grows big enough before switching so every iPhone feels fresh and remarkable from its predecessor.

4 -> 5S -> 7 -> XS -> 13Pro

Coming from SE1, I think 7 had the least wow effect on me and probably 8 could've been a better jump, although was an amazing phone with a lot to show compared to SE1
 
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My wife ended up cracking the screen of the iPhone 5s I gave her, and this is around the time that the iPhone SE1 came out. I got her the SE1 (and an Otterbox Defender case)
This story was a fun read. The Otterbox was a funny addition.
 
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Anything after the XS Max - Imo, that was peak iPhone. I regret getting the 13 Pro Max. The 14 Pro Max I have is nice, it's just getting too expensive and the features don't change much anymore. I even thought about selling my 14 and going back to my XS Max. It's sitting in a drawer.
So inferior cameras and screen in an old phone are more tempting than the most current thing?
You complain about features not changing much but think about giving the ones you got up for something less?
 
My iphone 5S was my first iphone. Not really bad but I found it too small from the beginning. Display was too narrow.
 
Similar to others, I wish I’d skipped the 7 and held onto my 6 until I got the X, but my younger self was chasing iPhone thrills.
 
definitely the 14 pro max for me right now

the 13pm might have been one of my favorite iPhones of all time. amazing battery life, the screen upgrade from the 12pm was night and day (12 had the yellowish screen cast, and no 120hz). in meaningful ways it felt like a nice upgrade from the 12 series

the 14pm does not feel meaningful. dynamic island was super clever when I saw the keynote but in use it's a mild quality of life improvement. the photos from the phone are not a noticeable upgrade as I rarely use the pro raw mode. and superficially I prefer the phone colors on the 13 series - the graphite and alpine green I like better than space black and deep purple.

plus subjectively my opinion is shaped by the fact that I had purchased a basically brand new green 13pm for a deep discount second hand on Facebook marketplace, so it makes it feel even more like I had no need to upgrade and had a perfectly fine phone.

all that being said I do like the 14pm and of the iPhone lineup this year this is the phone and color that I would upgrade if I actually needed the upgrade. but if I could go back I'd just hold onto the 13pm another year
 
Going from the black iPhone 4 to a White iPhone 4S.

Just in terms of cost and the fact a few months down the line I decided I didn’t like the white!
 
XS for me. I can’t say I’ve really regretted any of them but the X to the XS was very underwhelming

It was a very minor upgrade indeed. The regular XS didn’t fix the average battery life of the X as well.
 
Gonna have to say the iPhone 14 Pro Max followed by the iPhone 8.

I had a perfectly fine iPhone 13 Pro Max which I traded in because I got hyped up about the cameras on the 14 Pro Max and in my day to day use I hardly see much difference between them. Bearing in mind I don’t use RAW unless I see it fit for the occasion.

iPhone 8 as a device was at pinnacle of the home button era so it didn’t have anything to complain about but then we were moving to the all screen era and I didn’t want to take chance with the 1st gen of a new type of device.

In hindsight that’s exactly what I did with the 14 Pro Max and I’m not gonna say it was my best decision.
 
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To date the iPhone 12 probably. The battery was appalling on it and I’ve had a 4, 5, 6, 6S and 8 Plus prior to it.
Yes same, why is it like that?

I went from a 7+, have had the 12 for 18 months and the battery is bad.

Still a year or two before I upgrade :(
 
iPhone 6 Plus

That thing was underpowered since day 1. It had low RAM and a high resolution screen meaning it was constantly resetting apps and after a few updates it became notoriously slow and laggy.

Then the battery problems started. The phone would just randomly start shutting off somewhere from 30% and below, making it extremely unreliable.
 
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Going from 2005 to 2022 July without a cellphone was great!
so I dd not regret getting any iPhones.
 
I don't regret my 14 pro purchase, but I was disappointed with the sheer weight of the chassis, coupled with the ugly slab side design.
Putting a case on it made it even more bloated.
It does not ooze class and style like the X/XS; it is just one heavy slab.

That would all be forgiven if it wasn't riddled with little spurious usability issues... which could be iOS 16.
 
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I don't regret my 14 pro purchase, but I was disappointed with the sheer weight of the chassis, coupled with the ugly slab side design.
Putting a case on it made it even more bloated.
It does not ooze class and style like the X/XS; it is just one heavy slab.

That would all be forgiven if it wasn't riddled with little spurious usability issues... which could be iOS 16.
iOS 16 has been perfect and stable for me since release. I have been using it on the 12 Mini and 13. I think most of the complaints are from 14 Pro users due to Dynamic Island. It will probably take until iOS 17 to fully iron out all of the bugs.
 
iPhone 5, not well made IMO, the power button was faulty, known issue, and the chassis felt weak. Thats the one I ‘regret’ buying and using.

I did go through a time of owning the iPhone 7 2 or 3 times and an iPhone 8, but sold or sent them back as I just kept using my 6S and didn’t think they were upgraded enough to change. But I didn’t regret buying those though, I do still have my 6S in a drawer.
 
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XR...coming from 5S...it felt way too big for me to ever get comfortable with...I jumped on the 12 Mini as soon as I saw it and have been delighted ever since...

I thought that going from my 6S to the XR, trouble is my eyes love that bigger screen so I’ve been using it since I got it. Kinda got used to the size over time. I looked at the Mini and thought about it, but then looked at the Max next to it and my eyes are screaming Yes Yes Yes! So yeah, didn’t get a Mini lol. May go Max next.
 
iphone 4. i don't know why people called it 'death grip', just holding it normally would cause the call to drop completely for me.
 
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My biggest regret is the iPhone 6. The iPhone 5s I had before it was fine and only got the iPhone 6 because of the “hype”. Let’s be honest all the 6 had was a “larger” screen. Otherwise the A8 was barely an improvement over the A7 and Apple kept the iPhone 6 at 1GB of RAM which seriously strangled the device.

Also, iPhone 5C that I had for a couple of weeks before finally getting the iPhone 5s
 
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I wonder how much iOS 16 bugginess factors into regret for people on iPhone 14 variants

Also seems like a lot of “samey” vibes for people coming from 13 pro’s or iPhone 13 to 14 which is almost the same phone even same SoC
 
I wonder how much iOS 16 bugginess factors into regret for people on iPhone 14 variants
I am in the camp of ios bugginess.
Wife's upgrade cost us $480 - there is indeed no $480 difference between 13PM and 14PM. 13PM was buttery smooth, while 14PM i always see this freezes/micro lags everywhere.
I am sold for RAW quality for myself though.

But my 13, 13 mini never lagged when i want to quickly open the app from search menu - 14PM sometimes micro lags there, which triggers my OCD, because 13PM never skipped a beat.
 
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I regret upgrading from my X to the XS. I didn’t feel there was enough of a difference between the two to warrant upgrading but I already had soooo… lol.
 
I snubbed the X and had the 8 Plus and for me it’s probably the best iPhone I’ve had to date. Battery life was brilliant and it was super reliable in terms of very little software glitches. I still see them in use too whereas the X and XS are quite rare these days in my part of the world.
Several people I work with still use an 8 Plus. To this day I regret not taking over my wife’s 8 Plus when she was upgrading to the 11 at the time and she ended up trading it in.
 
iPhone XS. In some ways it was great coming from an iPhone 8, but the silver scratched like crazy and I had a BT issue that Apple wouldn’t address even with  care. Couldn’t wait to get rid of it.
 
My 12 pro max had like three different defects and the camera and screen were god awful. Even the LCD on the 11 looked better to me save for the low sharpness.
 
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