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Iphone 8 Plus was the biggest regret for me as it was short lived when the X came out.

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.
 
I'll give a different perspective: none, because I mostly have waited for a generation in between, so the changes always feel more substantial. For example going from a simple 12 to a 14 Pro Max, enough changes from a model to the other to be wowed by it.
 
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It was the 11 for me, upgrading from a 7. I quickly swapped with my wife's XS. She's still using the 11. I'm sure it was fine really, I just don't think I was ready for its size. Seemed a bit bulky.
 
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...
 
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iPhone XS Max was nice because of the size, but the camera wasn't great. The features weren't that great.
Much better than my previous 8 Plus, though.

11 Pro Max was awesome for the battery life and ultra-wide camera.
12 Pro Max was great for battery life, better cell service and RAM.
13 Pro Max was great for the 120hz ProMotion.
14 Pro Max is kind of meh. Thinner bezels are nice, dynamic island is cool, always on display is cool. 48MP ProRaw is useful for group photos. Not that game-changing though for everyday life compared to 13 PM.
 
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13 Pro, the one I currently have. Bought it for the camera. The 12 camera was actually fractionally better and the telephoto on the 13 Pro is terrible. The 12 also weighed quite a bit less.
 
All the ones I got for my kids, who seemed to view dropping them onto the hardest possible surface as a challenge.

As for me—I’ve been a user since the first iPhone. Though some have been better than others, I’ve never regretted any of them.
 
Well, my previous iPhone is the 7 Plus, so that’s the only one I can comment on 😂

I didn’t regret it when I bought it. I bought the black matte color, and it’s just gorgeous. Love the curved design and feel. IP67 is also a huge plus for me. And it’s so thin compared to most phones nowadays.

But at its last days, the overheating and crapshoot battery life really got into me. It’s difficult using the phone full time. It’s a relic of iPhone past where everything was simpler.

I wonder what would happen if Apple keeps making these older SoCs but with new fab, ie the A10 with 4nm
 
12 pro max. I got rid of my xs max. I think I could have gone another year with the xs max. Comfortable to hold.
 
IPhone 11 Pro Max - that thing was gargantuan. I don’t even use a case, and it was still just… huge. I’d come from the X and almost immediately missed the smaller size. I stuck with it for a while, finally got an iPhone 12 Pro and was MUCH happier with that.
 
12 mini. I returned several because they all had screen issues. Waited until the 13 mini was released, which I now own and am completely satisfied with.
 
iPhone 14 Pro followed by the XS (both with utterly intolerable OLED screens) and maybe iPhone 12 (solid device, just didn’t really need to upgrade from my 11 at the time).
iPhone 4 was quite a doozie. The least excited I ever was for a new iphone was definitely in the last few years.
 
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I've owned a 4, 5, 6, and XS Max. Used a 5s and Xr for work so they were free.

Probably the 5 if I'm honest. Minimal change from the 4. 6 was the first phone that felt like it had a normal sized screen so that was a pretty big deal. Still rocking the XS Max. It's been a workhorse.
For this reason, I bought the “s” version whenever possible, 4s, 6s.
 
While it’s a great phone overall, I did end up regretting my purchase of the 12 Mini. The 8 I had was running perfectly fine and only required a battery replacement. The battery life was completely underwhelming and I required a MagSafe battery pack to last the day. I normally keep my older phones as part of a small collection however I ended up selling it for a surprisingly high amount due to the perfect condition it was in.
 
While it’s a great phone overall, I did end up regretting my purchase of the 12 Mini. The 8 I had was running perfectly fine and only required a battery replacement. The battery life was completely underwhelming and I required a MagSafe battery pack to last the day. I normally keep my older phones as part of a small collection however I ended up selling it for a surprisingly high amount due to the perfect condition it was in.

That’s unfortunate. What did you end up getting?
 
I had many different iPhones which I mostly bought second hand, selling the old one, whenever I wanted to try another model. Did not cost a lot of money, just a lot of time ;)

Anyway, I regretted getting the 8 over the 7 most. I did not make sense to upgrade to a phone that was basically the same but slightly thicker and heavier with a glass back, and I loved having the Jet Black color. So I ditched it quickly and got a Jet Black 7 Plus.

XR an 12 were underwhelming also, coming from 7 Plus and XS. Both felt too big and heavy which I why probably my current 13 Mini feels like a great choice.
 
14 Pro Max. Wish I’d hung on to my 13 Pro Max. Got on better with the camera system on the 13 PM and the battery health was still 100% when I sold it after 12 months. 14 PM at 99% by Jan ‘23 with exactly the same usage and charging routine. Suspect the battery in the 13 PM was bigger than spec‘d though - so it just seemed that it was degrading slower….
 
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Probably when I upgraded from a 3G to a 4. It felt like a beta for what the 4S would become.
 
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I remember the feelings so clearly….

It was the 5s and the XS that I hated. The 5 situation was simple; I missed the slate black of the 5. I bought a white XS which turned out to be the only time I stuck with a non-dark variant phone. On top of that, the battery was horrendous and my wife dropped it and smashed the back glass.
 
iPhone 7. I came from the 6+ and loved the smaller, more ergonomic size at first but quickly noticed how much having a smaller battery and screen made a negative difference in day-to-day life. I sold it after a few months and got a 7+.
 
14 Pro Max. There is a limit to how heavy a slab iPhone can be to be used comfortably IMO. The heavier the worse at that size. I'm also so over phones that large. So much happier with the regular 13.
 
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this is an interesting unique thread, I like it!

14 Pro Max. There is a limit to how heavy a slab iPhone can be to be used comfortably IMO. The heavier the worse at that size. I'm also so over phones that large. So much happier with the regular 13.

I think 15 pro's are gonna be worse with the bigger camera unless they have titanium up their sleeve

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I think I regret 4S to be honest. Mine would randomly shut off and the screen was horrendous I lost the lottery and I didn't feel like going through a warranty loop for whatever reason at the time. Also not as hackable as an iPhone 4 that had limera1n. Siri was a novelty but still kinda overrated at the time (and currently, imo). Battery life was way worse with A5 than A4. It was a step forward, but a couple steps back. Way more performant but at a cost.

Otherwise don't think I regret much

OG -> 3G -> 3GS -> 4 -> 4S -> 5 -> 6 -> 6plus -> 6sPlus (and SE1 I think?) ->7Plus -> X -> XR -> SE2 ->12Pro -> 14PM

Slightly regretted 6 since I had it for a month and then sold it and got a 6 Plus. Went phablet route for a while.

Would say I regret X to XR going OLED to LED but that would be a lie since the battery life was stellar and I liked the 6.1" size at least coming from 5.8"

Overall no regrets
 
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