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The 6. I was coming from the 5 and should have waited for the 6S which had extra signal bands for T-Mobile that my 6 didn't. It also had 3d touch, but I didn't use it much other than moving my cursor via the keyboard. #2 was the 8 Plus...it was too big.

3 -> 4 -> 4S -> 5 -> 6 -> 6S -> 8 Plus -> 12 Mini -> 13 Pro

I don't plan on upgrading again for a looong time.
 
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Buyer's remorse? none, and including everyone in the family we had 3GS, 4S, 5C (?), 5S, 6S, 7, X, XR, 11PM, 11, 13PM, 13mini ...
 
The XS. Mainly because it offered so little from my 1-year old iPhone X. And I loved the iPhone X - it's the only time I've gone with a color other than Space Grey because some how it just looked right in Silver. I got the XS in Space Grey and immediately regretted it.
 
No iPhone complaints, but I do regret buying the 4th-gen iPod Touch. I got it about 6 months before iOS 7 came out and was disappointed to find out that my essentially brand-new device couldn't run it.
 
I traded in my 12PM and got the iPhone 15PM. I regretted it the first two days. My iPhone 12 Pro Max was long gone. I purchased a 14 pro max with Att’s deal. I find the 14 pro max faster than my iPhone 15 pro max. Idk why but I feel like the iPhone 15 pro max stutters and it feels clunky. I have put them side by side and the 14 feels so much smoother. Hmmm ¯\_(ツ)_/¯
 
I've had every phone since the 5 and no regrets. I did exchange one because of an uneven screen. I did not regret getting the 14 Pro Max, but found it too big and heavy and am back to a 15 Pro this year which is perfect for me.
 
not an iPhone, but it was a Samsung Omnia 7 one of the very first to run the Windows Phone OS which promised much as an OS but ended up being total crap with limited 3rd party app support. I got this as my phone about a year after I bought the 3GS...... I quickly went back to the 3GS.
 
The 8 because it felt so similar to my 6, but less premium with the glass back. The 6 is the iPhone I've loved the most but it was also my first.

The 13 Pro because it was so heavy and I felt the shiny stainless steel finish looked so chintzy.
 
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I liked all of my iPhones.. 4S, 5S, 7, XS Max, and now 14 Pro.

I disliked the 7 the most though. I had issues with voice and audio, I had a couple of 5S replaced due to heat from work would warp the phone in my pocket.. whoops. I think they make a pretty good phone, and OS to go with it.

I really dislike spending 1K+ on a good phone though.
 
My experiences have all been good - no remorse. Started with the 3g, then the 5s, 6s Plus and finally 12 Pro Max which I'm still using. Each of these was a nice upgrade from my previous phone. If I had upgraded more frequently, I'd probably have some regrets though.

Planning to stick with the 12 Pro Max for another year or more. Really not much of a "phone person" these days and it meets all my need just fine. :)
 
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I’ve only had iPhones since the first one and I’ve always been thrilled. No buyers remorse whatsoever.
 
For me it was the iPhone 6. It was my first smartphone and it was so slow, I couldn’t stand it. It just made me frustrated, so I gave it to my spouse.

Got the 6s when that came out and that was light years better.
 
iPhone 5C and iPhone 12 mini.

iPhone 5C is overpriced for what it is and the plastic back is fingerprint magnet.

iPhone 12 mini has horrible battery life.
 
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The biggest regret I have ever had was that iPhone 7 as it was continuously having issues from the first week. I ended up having it 9 months and went with a iPhone 8 on the first day they had one. Name an issue and that phone had it, everything from a cracked screen to hardware issues with the camera and a failed battery after 4 months I had them with that phone. I normally had a 2-3 year upgrade so I went from a 3G then a 5 and then that horrible 7 then a 8 then a 11 Pro, a 14 Pro and then the 15 Pro I have today.

Secondary issue with the 14 Pro was my mistake as I should got more storage then base storage, no real regret on that just a mistake I made. I went with 512 GB storage on the 15 Pro.
 
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