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For me, the biggest technological (and possibly design) jumps were:

iPhone
iPhone 4
iPhone X

Both in terms of design and technology that came they really blew me away the most. In a sea of windows mobile, palm and blackberry smartphones, picking up and using the iPhone for the first time with a capacitive display, multitouch and such an interactive OS just really blew my mind. Still remember the Apple Store and table I stood at when I attempted to dial a number on the keypad after being frustrated at doing the same on a resistive touch screen windows mobile device for the year before.

iPhone 4 was next - really timeless design with the steel frame and glass back, and going to that hi dpi screen just felt like another level.

iPhone X felt like a similar jump, almost like the original, just going back to how we first used an iPhone by picking it up and sliding to open. Stainless steel body feels incredible as well, and seeing the screen fill all four corners of the device with OLED just looks gorgeous.

I've owned every iPhone since the original, but those 3 really felt like the most significant along the way.
 
. . . If am forced to pick, when they went to the 3G. Before then, the previous iPhones just lack the power to run the software, often freezing up, people looked at those 1-2 gen iPhones as no more than toys, they kept their Blackberrys for everyday, "serious" tasks. 3G had enough power for users to take a second look.

This is it!

The move from EDGE connectivity to 3G.

After seeing the EDGE iPhones in action, I refused to buy one as it was so slooooooooooow!

My first iPhone was the 3G, followed by the 3GS etc etc
 
Support for textmessages (SMS/MMS/imessage), icloud backup and restore, appstore, airplay.


Ohhh, and not to forget, multitasking :)
 
I would have to say the first iphone, it introduced multitouch to the mainstream world, changed the world and killed off the hard keyboards. Everything else has not really been a game changer, probably 3GS with apps was also big and 5S with touch ID was cool too. But everything else has lacked any real wow factor.

The 3G came with apps. The 3GS (which I didn't buy) was the first one that Apple deemed good enough to support for multiple years. Looking back, I see that after the 3GS came out Apple still sold the 3G for at least a little while. But OS support was only for 2 years. Apple finally realized they could do multi-year support, which still remains a distinguishing feature for Apple vs most Android phones.
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This is it!

The move from EDGE connectivity to 3G.

After seeing the EDGE iPhones in action, I refused to buy one as it was so slooooooooooow!

My first iPhone was the 3G, followed by the 3GS etc etc

I bought the 3G halfway through it's first year when I was finally eligible for an upgrade through Apple. I had bought a Treo after the original iPhone was announced, and before it was released, due to the limitations of the phone at the time (no apps, 2G only, price). 18 months later I bought the 3G (apps, 3G). I was also used to the Windows mobile system.

Of course, in the 10 years since, I've become less rigid in price, spending $1150+tax for a phone :(
 
My picks would be the iPhone 4 (that all glass form factor and retina screen) and the iPhone X.

I guess iPhone 6 bringing the Plus varian in was pretty great as far as change goes too, but that wasn't necessarily a technological leap.
 
The iPhone 6s was a major step forward. While it may seem minor, its improvements were highly significant.

2GB Ram
3D Touch
12MP Camera
7000 Series Aluminum

The next in line would probably be the X. Face ID is an interesting new method of unlocking your phone, but it's not major enough to warrant the top spot. Also, the glass design was done 7 years prior with the 4. Next is the 3G which introduced the App Store and 3G LTE.
 
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The iPhone 6s was a major step forward. While it may seem minor, its improvements were highly significant.

2GB Ram
Force Touch
12MP Camera
3000 Series Aluminum

The next in line would probably be the X. Face ID is an interesting new method of unlocking your phone, but it's not major enough to warrant the top spot. Also, the glass design was done 7 years prior with the 4. Next is the 3G which introduced the App Store and 3G LTE.
3D Touch.
 
The iPhone 6s was a major step forward. While it may seem minor, its improvements were highly significant.

2GB Ram
Force Touch
12MP Camera
3000 Series Aluminum

The next in line would probably be the X. Face ID is an interesting new method of unlocking your phone, but it's not major enough to warrant the top spot. Also, the glass design was done 7 years prior with the 4. Next is the 3G which introduced the App Store and 3G LTE.

There is _No_ 3000 series aluminum, there was the 6000 series which was used for the iPhone 6, then Apple transitioned to the iPhone 6s starting using the 7000 series aluminum, which is much stronger and is also used with the Apple Watch.

Also, as Shanghaichica mentioned, you missed 3D Touch, which was a fairly large upgrade to the iPhone 6s and changed dynamically how to interact with the iPhone.
 
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You guys are completely right. I typed this before I went to bed. Whoops... post editied!
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There is _No_ 3000 series aluminum, there was the 6000 series which was used for the iPhone 6, then Apple transitioned to the iPhone 6s starting using the 7000 series aluminum, which is much stronger and is also used with the Apple Watch.

Also, as Shanghaichica mentioned, you missed 3D Touch, which was a fairly large upgrade to the iPhone 6s and changed dynamically how to interact with the iPhone.
 
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