It's pretty important to user satisfaction that Joe can say to Sally "You have an iPhone, right? Check out what they can do now!" And Sally be able to say "Mine does that too? Awesome!"
As opposed to Android, where Joe and Sally can barely help one another through the various UI skins half the time, let alone share enjoyment in cool new software features on devices purchased mere months apart.
(Sure, with iOS there are updates and features that don't get patched into older devices. But those situations are vanishingly few compared to Android.)
So, as an answer to the various times this question has been posed in this thread: Yes. It's a big deal to normal users that reasonably contemporary devices behave the same and generally have the same software features. And it's a very big deal for them to find out they bought the 'wrong' phone, not six months ago, because they got a model that will likely never get the cool new software feature their friend just showed them.
The degree to which updates don't matter, is the degree to which the users are barely interested in the device at all and use them as little more than a flip phone with better email and browser.
Which, while accurate for a certain population of users, hardly supports the relevance of any possible Android feature advantage.
Sally won't be able to do Turn by turn if she has a 3GS or iPhone 4, whereas even out of date Android's on 1.6 can.
The situation is much more nuanced than you state.
I would argue that as new features in newer versions of operating systems become more and more of a spectacle that people everywhere, not just geeks are watching, Pushing major OS updates becomes more and more important.
If you're going to show off a new feature to the world, it's nice if most people can actually get at it.
No, but only the really low-end Android phones are coming out with 2.x anymore and that number is going to dwindle quickly over the next year. And ICS is not as crucial as some people make it out to be since 2.x is a decent platform already and a lot of features have been backported.
I can't agree with that. Many felt that way in 2006 and definitely turned out not to be the case.
Like I said, no fundamental changes.
Agree that notifications pull down and similar are gravy, but tasty gravy nonetheless.
Yes, but how important is this really in practice? With both platforms approaching maturity deploying major OS updates OTA is going to be less important.
Google can ride the natural device upgrade cycle to get out new versions. If they can make the browser and email client and a few other key apps independent of the OS they can rev those a lot faster. No doubt they'd like to have Apple's upgrade muscle but I'm not convinced they really need it in the long term.