Which of the Android upgrades is a more significant milestone?

1.6-2.1, although I haven't been using any devices earlier than 1.6.
Eclair changed so many things that really made android usable (as some others have said)
Voice commands.
Much better keyboard that was an annoyance in 1.6

But for many the most important introduction was the betterl support for more screen resolutions. For example, we who had the Acer Liquid which had a 480X800 (WVGA) resolution but initially ran 1.6 which meant that everything got much better with the new support for WVGA in 2.1.

Live Wallpapers were also introduced and it is something we take for granted today and although I fell they can be gimmicky, they still are just one of the more obvous things that really separates android from ios.
And the whole OS felt much faster than in 1.6, not to mention much less buggier, more than any version upgrade since!
And there were loads of other things introduced (I think Turn by turn GPS also was introduced).
And the icons changed from the Ugly semi-3d look to a much better and fresher look.
The drawer for stock android also looked significantly better than the ugly 1.6 one (I hope most agree on this).

For me, at least, it has been the upgrade that made the greatest difference!
And it was around the time when android started to grow beyond the "cut-off point", mostly thanks to the Motorola Droid which was the first device with Eclair (though the 2.0 version) and later the HTC desire.
All on Eclair.

I have a x10 and we have seen from 1.6 to early 4.0 and honestly i can say from experience that 1.6 to 2.1 is by far the more significant

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I had an iPhone for years and wanted to go to android but nothing really drew my attention, i didn't really like the look that android had, it didn't really seam polished. Fastforward a year and a half later and then 3.0 comes out and i go "Hmm this looks pretty nice and pick up a TF101. Then a year later i see the Galaxy Nexus and the beauty of AOSP and went "wow this looks beautiful, and AMOLED wow this looks like one awesome device" now I have a Nexus.

So i would say 4.0 is the major milestone it attracted me and it really made android beautiful

My first device was the MT3G and after using that on cupcake, and donut, then upping to an eclair build I would say that was a huge upgrade in looks and functionality.

2.3 to 4.0 when Android becomes fully mature, beautiful and even greater iOS competitor.

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I have been on Android since 1.5,with my then new and shiny HTC Hero,all the way to 4.0.It's been a hell of a ride,that's for sure.I still remember the day when my Hero was updated to 2.1(VillainRom awesomesauce ),it was the first thing to really replace my iPod Touch.
But still,I'd say that the most significant transition is 2.3->4.0.Not because of functionality,and not only because of looks and the fell of it,but for all of these together.Android finally works.Period.Don't take me wrong,I've always loved Android.And its faults were what drew me to it initially.I was eager to learn and loved customization.Each thing I fixed had taught me something in the process and helped me make the phone really mine.But 4.0 allows for all that only for the pleasure of it.And that is the best that could happen to it.

I have to say 2.1 to 2.2. The JIT Compiler and other dalvik optimizations really made me stick to android.

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I think 2.3 to 4.0 is huge leap, in terms of user usability, 2.1 to 2.2 in terms of performance.

syonatha said:

I think 2.3 to 4.0 is huge leap, in terms of user usability, 2.1 to 2.2 in terms of performance.

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Aesthetics Wise 2.3-4.0 Performance wise 1.6-2.1

It is hard to say since it is so device dependent. My P1000 Tab performed significantly worst when updated from 2.3 and same for the milestone from 2.1 to 2.2

In terms of usability, I think 1.6 to 2.x is a big jump for me. Just checking out 2.x to 4.0 now and I don't feel it is any big improvement. May be hardware limited. Will wait for my 3.2 to 4.x upgrade to judge.