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For just myself, not counting phones I've bought for others I'm at:

iPod touch (2nd edition) (not a phone but I count this because I used it as a phone, albeit one tethered to my BlackBerry)
iPhone 3GS (2 - I left one in a cab, bought a new one and then had a kind person find it in the cab across the city of Miami and mail it to me, leaving me with two)
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
iPhone 12 Pro Max
iPhone 13 Pro Max
iPhone 14 Pro Max
iPhone 15 Pro Max

So I've owned every model year except the original (and I was in college and thus too broke and too against AT&T to switch) and the iPhone 3G (just graduated from college right as it was released but still too broke to switch to AT&T, but I did buy an iPod touch that I used similarly as a phone).

I will obviously be buying an iPhone 16 Pro Max in a few weeks.

My favorites are probably the 4/4S (best design/size and the 4S which was actually available in white), the 5 (LTE meaning I got to switch to Verizon), the 5S (TouchID), the 6S Plus (rose gold), the X (design), the 13 Pro Max (chamfered edges and fixed battery life, thank you) and I guess I'll give a nod to the 15 Pro Max (USB-C, 5x optical zoom).

My least favorites, probably objectively the 3GS (even though it wasn't a bad phone, the 4 was just MUCH better), the 7 Plus (which was a fine phone, the software was more the issue), the XS Max (superfluous and little reason to exist, aside from its larger size compared to the X), and the 12 Pro Max (battery life issues that I blame on that years version of iOS).

It's funny, I have very small hands so you think I'd prefer the smaller phones (and in theory, I do), but because I want the latest tech, the iPhone mini is out and even the smaller sized pro phones require I use two hands, so I get the Max units for more battery life, since I have to use two hands anyway. I just get a purse-type case for occasions when I'm wearing something without pockets and have a clutch that is too small for my phone.

I either trade my phones in as part of the upgrade program or hand them down to my spouse/a friend or sell them at a discount to a friend in need. This year, I'm on the upgrade plan but I sort of want to keep the 15 Pro Max around as my secondary camera, so we'll see. I might pay off the loan and start another one or just buy the 16 Pro Max outright, depending.
 
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and I also hated my 6S Plus (way too big).
Same. I hated the design of the iPhone 6 as soon as I saw it, but decided to try the 6s Plus for the size.

I thought I would like the larger size, and I guess I did, but only when I could have two hands holding it. Considering 95% I was trying to one-hand the wannabe iPad, I quickly started to hate the size.

It was very hard for me to take one-handed photos and videos, it was frustrating.

I had no place to put it in my cars due to the large size. I would place the 6s Plus on the passenger side seat, and sometimes it would go flying off the seat when taking a turn too sharp.

When I started shopping for clothing with pockets that would accommodate the large phone, I knew that I had to get rid of it.

It was the only iPhone that I sold, and I still have all my other old iPhones.


4S was also my favorite (followed closely by 5S/SE1)
I never realized how much I love the 5S and SE1 until I bought my wife an SE1 after she cracked the screen of my 5s that I gave her. I gave her the 5s after she cracked the screen of her iPhone 5.

I bought my wife the SE1 when they launched and also bought her an Otterbox Defender case (so she would stop breaking them). When setting up the screen protector and Otterbox case, I remembered being envious of the small and really light SE1 when I was holding it. I wanted to buy one that day for myself, but I didn't want to drop my storage from 128GB to 64GB which was the largest storage for the SE1 at the time.

I think it was about six months later, Apple launched the SE1 with the larger 128GB storage, and I bought it right away and sold my iPhone 6s Plus. The Touch ID 1 was slower, and the battery life was a little worse, but I loved the size of the SE1 and would have kept it still today if it wasn't for the slower chip.

I would have gotten 13 Mini too, but I opted for SE3 because it has Touch ID. Really frustrating the size of phones these days.
I was on the fence for the same reason as you, Touch ID. I wanted Touch ID, but didn't want the larger size of the SE3. I went with the smaller 13 Mini. I would still prefer Touch ID, but the Mini is a good size, maybe a little too big, but at the time it was the smallest option.
 
I can’t believe it but I’ve had 21 iPhones…

3GS
4
4S
5
5S
5C
6
6 Plus
6S
6S Plus
7
7 Plus
8 Plus
X
Xs
Xs Max
11
11 Pro Max
12 Pro Max
13
15 Pro Max


Fortunately I managed to kick that incessant need to get a new phone (or 2) every year.
 
I’ve gone:
  • 3G
  • 4
  • 6 Plus
  • 7 Plus
  • 8
  • X
  • XS
  • SE
  • 11
  • 12 Mini
  • 12 Pro Max
  • 13 Pro Max
  • SE2
  • 14 Pro Max
I don’t think I’ve missed any 🤔

Always regret never getting the 5 and 5S (also had about 10 Android phones in between some iPhones)

Two favourites were the 4 and the X, as they both really represented a quantum leap compared to the competition. I remember being in a Windows Dev company on the day the 4 was announced and everyone being blown away by the Retina display and the fit and finish.

Very similar experience when the X was launched, just a “money is no object” piece of hardware (very similar, I assume, to the Vision Pro)
 
Three!

iPhone 5
iPhone 6S
iPhone 11 Pro

I switch when there’s an issue.
 
Here’s a question. Will any of these iPhones become worth anything in the future? My parents have upgraded so I’ve got 2 fairly mint iPhone 5’s but currently showing a £30 value..
 
Original, 3GS, 4, 4S, 5, 5S, 6, SE(2016), 6S?, 7+, X, 12 mini, 14 Pro. No plans on upgrading this year.

I think in those early days, yearly upgrading seemed like you were getting a lot more every year from a speed and performance standpoint, as well as features - I was also young and had a lot more disposable income. I was very happy with my 12 mini, but I wanted to upgrade so I can also replace my iPad, camera, ebook reader, etc. Which my 14 Pro became my main thing for each of those replacements, though I really do miss the mini size.

If I had to say my favorite, I'd probably go with the SE (2016). I can’t remember exactly the timeframe, I know I bought one at launch, sold it, possibly upgraded to a 6S or went back to using my 6 for a while and rebought an SE (2016). Unfortunately, I no longer have that SE, but still have my old 5 which I pull out once in a while. Which has a broken lightning port so I never bothered selling it. I just love everything about the size and look of it. The aluminum back flanked by the glass edges, being able to actually use it with one hand (the mini is still a little too big for me).

As much as I keep on eyeing the 13 mini whenever it pops on to the Apple Refurbished store, and as much as I keep telling myself I really want it. I’m happy with my 14 Pro for the reasons I listed above, a device that can replace other devices I regularly used. With some tasks, I wish it were smaller, others I wish I had the Pro Max. So it's a nice middle ground.

My launch day 14 Pro still looks and works like it's brand new. Unless something catastrophic happens to it within the next two years, I probably won’t upgrade until at least the 18 lineup comes out. If I want to go out with a smaller device, I'll just use my Apple Watch on cellular and leave my phone at home.
 
7 iPhones. My first iPhone was the first iPhone, my current iPhone is the 15 Pro.
My favorite iPhone (by far) was the X. It was perfect - the design, the size, the redesign at the time. I loved it so much. I kept it for 5 years (the longest I have had an iPhone). Then I got the 13, which was okay... The best thing about it was the better/new battery, but other than that, I wasn't a big fan of the slightly larger size and new design. And honestly, I'm a little disappointed in the 15 Pro as well. The battery life is not good at all, and it overheats so often just doing basic stuff.
 
I've only owned one, a 3GS.

I've been more interested in trying out different hardware over the years, which is why I've been on Android handsets since my three-plus year run with my sole iPhone. But I'm considering picking up a 16 Pro at the end of the year and tying my Mac and iPad together with it into a small ecosystem. I'll still keep an Android phone and Windows laptop, but I'm ready for a bit of day-to-day continuity/fluidity of use between my primary devices.
 
5s, 6s, 13, 15 with breaks between the 6s and the 13 when I had Galaxies and Pixels. Loved them but wanted to come back to the iPhone when they raise the base storage and with the 13 they finally did. The 6s feels like it's lived on forever. Still a usable device apart from the horrible battery life.
 
4, 5, 6, 7, XR, 12PM. I used to be an every second year guy, but the 12PM has been super solid for me and does everything I need. After 4 years the battery is still at 88% and I could keep it another year, but I’m getting the itch so I think I will get a 16PM.
 
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iPhone 3G
iPhone 5
iPhone 7
iPhone 8 Plus
iPhone 12 Pro Max
iPhone 13 Pro
iPhone 14 Pro Max
iPhone 15 Pro Max

Favorite phone was the iPhone 8 Plus. I loved that phone and kept it for a long time in the old Speck grip cases. It felt great in the hand, and even thinking about it now, I miss the old home button at times.

I can’t say I have really regretting any iPhone purchase [there were quite a few forays into the Android world I definitely regret], but going to the iPhone 13 Pro from the Pro Max was difficult. I am thinking about trying again, but that battery jump is a head shaker.
 
iPhone 5
iPhone 6 Plus
iPhone 7 Plus
iPhone 12 mini
iPhone 13 mini
iPhone 15 Pro Max

My favourite was the iPhone 5, perfect size and I love the design. While the mini’s are great and I like their size, they’re still too big for me so I figured since they won’t make anything smaller, may as well get the Pro Max since I’ll always find the iPhone too big lol
 
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1. iPhone (OG; 2007)- Briefly owned but I'll claim it anyway. Traded a friend my Motorola RAZR and some cash, then traded back. Long story.
2. iPhone 3G- first iPhone I actually kept.
3. iPhone 4
4. iPhone 5
5. iPhone 6 Plus
6. iPhone 7 Plus
7. iPhone X
8. iPhone XS Max (lost)
9. iPhone SE 2 (temporary)
10. iPhone 12 Pro Max
11. iPhone 13 Pro
12. iPhone 15 Pro
13. iPhone 16 Pro Max (likely)

The thrill of the original iPhone and 3G were unmatched but the Phone 4 was my favorite until iPhone X. All of these felt truly revolutionary. The 13 Pro was great as well- great size and battery life.

My least favorite was the 6 Plus, which was slow, the battery life was mediocre, and it was highly cumbersome. A close 2nd is actually the 15 Pro- downright terrible in every regard. I especially hate the battery life and thermals- I can't wait to get rid of it for the 16 Pro Max.
 
3GS
4
5
6 Plus

[Android]
XR
[Android]
12
13
15 Pro

15

The 3GS was awesome: I was looking into getting a 3G in late 2008, but decided to hold off based on the rumours of a new model. I think for many, the first few devices were like: "Wow, is this a phone?!".

I suppose my favourite was the iPhone 4. Literally every area was improved. It felt so luxurious, the display was awesome, incredible performance, etc. It also came out during a time when many people did not own a smartphone. I remember lots of people wanting to look at it and try it out. And I also remember some people saying: "Who needs something fancy like that? A phone is used to make calls!" (Yes, those people all own smartphones nowadays).

The 6 Plus was... not so good. While the regular iPhone 6 did okay (and is a favourite for many, I think, because it was the first time Apple really offered 'big' displays), the 6 Plus's performance was bad, due to its bigger display with higher resolution. This was the first time you'd really noticed Apple skimped on the amount of RAM, and the result was an endless reload of apps, safari pages, etc. The design with its big bezels also didn't really do it justice. It actually pushed me away from the iPhone for a couple of years.

After a few years, I got the XR. I didn't want to go for the 'X' as the price at the time was too extreme for my taste. The XR seemed a decent alternative. The XR offered a good experience, but now I was used to high-end Android devices with OLED displays - so I decided to return to Android. Until...

Finally, the iPhone 12 came out and was pretty good! It was the first 'affordable' iPhone with an OLED display. For the first time since the 6 Plus I was thinking: yes, Apple's back with a 'good value for money' iPhone. This phone finally was the right balance between premium hardware, price, design, new features, etc.

The 12 --> 13 upgrade and 15 Pro --> 15 downgrade basically fall outside my regular upgrade cycles, but I did it because it actually saved and/or earned me money:

I got the 13 only because the cost was fully covered by trading in my iPhone 12 (effectively costing me $0, while getting an upgraded phone with new warranty). Special carrier promotion.

The 15 Pro is pretty good and fell in my 'regular update pattern'. Eventually, though, I got a regular iPhone 15. I liked the Pro, but I had to upgrade my carrier plan due to some changes. They had a really good trade-in deal, while simultaneously having the regular iPhone 15 on a flash discount sale. After all was said and done, it basically earned me $400. I like the 15 Pro's extra camera and ProMotion Display, but they're not worth $400.
 
Think this is fairly accurate...

Original iPhone
3GS
4
5s
6s
7 plus (probably least favourite because of size but now I love the Pro Max versions so go figure!)
X
11 Pro
12 Pro Max
14 Pro Max

Planning to upgrade this year to 16 PM.
 
3GS -> 4s -> 5 -> 6 -> 8 -> 11 -> 12 -> 14 Pro Max + 13.

The 12 was a company phone that I only had for private use, and the 13 is my current company phone.

The best one? Probably the 3GS because I loved that thing and it’s the only one I still have. Worst one would be either my 5 (impulse purchase that I regretted buying until I got my 6 since the 4s was great) or my current 14PM due to the shear size of it.

I’ll hold on to the 14PM until it’s completely useless and/or broken, so next phone would probably be an 18 Pro or even 19 Pro (no more max for me!).
 
iPhone 4S was my first one in high school.

Then I had a several years in android with HTC/Nexus/Pixel phones.

Switched back to iPhone with the iPhone 13 Pro.

Currently have a 15 Pro. The 15 Pro is definitely my favorite phone to use of all time. Premium hardware, USBC, Dynamic Island, Action Button, 120Hz/AOD display. I'm very happy with my hardware and I don't really have a reason to upgrade this year since I get AI stuff to try out (not sure I'll use it very much but hey, worth a try I guess).
 
OG iPhone, 3GS, 4, 5, 6, numerous SE’s over the years, a 7Plus, an XR, an X, 11, 11 Pro, 12 mini, 13 mini, 13 Pro, 14 Pro and my current 15 Pro.

Think that’s me…
 
5

- 4
- 5s
- 8
- SE2 (insurance replacement of 8)
- 13 mini

I probably liked the 5s most.
 
This is fun!

My history:

iPod Touch 2nd Generation
iPod Touch 4th Generation
iPhone 4s - black 64GB
iPhone 5 - black 64GB
iPhone 5s - Space Grey 64GB
iPhone 6 - Space Grey 64GB
iPhone 6s - Silver 128GB
iPhone 7 - Silver 256GB
iPhone X - Silver 256GB
iPhone XS - Silver 512GB
iPhone 11 Pro - Silver 512GB
iPhone 12 mini - Silver 256GB
iPhone 12 Pro - Silver 512GB
iPhone 13 Pro - Silver 1TB
iPhone 13 mini - Starlight 512GB
iPhone 14 Pro - Silver 1TB
iPhone 15 Pro - White Titanium 1TB

My favorites were probably the X, the 13 mini and the 15 pro.

My only upgrade I “regret” was going from the X -> Xs. In the end, it wasn’t really worth the cost of upgrading. Yes the Xs was much more computationally advanced, it wasn’t until years later where the features started being added for the A12 and newer.

As of right now, I am planning to break away from the yearly upgrades this year. Unless there is some exclusive software feature, I haven’t found a reason to upgrade to the 16 Pro based on the rumors.
 
I had the 3G, 4, 4s, 5s, 6s, 7, XR, 11, 12 mini, 15.

The one I regret not buying was the Xs. The store convinced me the Xr was the better buy and soon there after I regretted my choice but it was too late and I was stuck with it. The Xs was by far the best iPhone and if they brough the Xs back again I'd go buy one tomorrow. I sure miss those curves.

The one I do regret buying was the 12 mini. That phone was utter trash. A battery I had to charge 3 times a day that was down to about 85% health within 6 months and they would not warranty. It fit in my pocket great but was otherwise awful at just about everything.

I'll likely stick with the 15 for a while as nothing I've read about the 16 excites me enough to spend money. There is less and less in the way of upgrades each year so you basically have to skip a few for it to be worth it.
 
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