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The thing is that the overwhelming majority of iOS users is usually at the latest OS version after a while and most of the rest are at the second oldest, after that the usage percentage drops off a cliff:

https://david-smith.org/iosver...

For Android users the picture is different, only about a third of users is at the latest version with the rest being at older versions:

I thought I saw on Apple's keynote that only 0.2% of Androids are on the latest version (7). Nowhere near 1/3 using latest version.

Security is always a moving target. While it's possible your leading edge phone is as secure as the leading iphone, what matters to security is how many people are running an older OS. Androids are always going to be running non-updatable OS just because of the bussiness model. So in terms of numbers of exploitable phones, swaths of the andorid ecosystem will be less secure than Apple ecosystem.

The thing is that the overwhelming majority of iOS users is usually at the latest OS version after a while and most of the rest are at the second oldest, after that the usage percentage drops off a cliff:
https://david-smith.org/iosver...
For Android users the picture is different, only about a third of users is at the latest version with the rest being at older versions:
http://www.droid-life.com/tag/...
This is to be expected since Android is open source, it gets used by a whole slew of manufacturers and while you can point to ones that do a good job with updates like Google it self or a somewhat reasonable one like Samsung (have had some bad experiences with their orphaned Android devices), there is a vast number of Android device makers that either orphan devices or drag their feet excessively with updates or just orphan devices as a matter of course. So while there are manufacturers that do a bang-up-job of keeping their Android devices secure, making shure the the entire Android fleet can match the update stats of iOS is a practical impossibility the way things stand at the moment. The only way to really change this is for Google to make sure that the underlying OS is provided by them, updated from their servers and the device manufacturer only gets to mess around with the GUI. If the manufacturer wants to make changes to the underlying system Google has to make them sign agreements obligating them to implement a certain protocol guaranteeing QA and that they will push regular updates over the lifespan of the device. Unless they do something like that the reputation of Android will always be ruined by sloppy device makers who drop the ball on security.

Very. I didn't wear a watch when I went to bed before, and the Apple Watch isn't changing that habit*. I have a cheap little charging stand that lets me use the watch as a bedside alarm clock while it's charging, so it's still useful even when I don't have it on. Charging overnight, like I do with my phone and laptop, is a non-issue of an inconvenience.

*David "Underscore" Smith made the Sleep++ app and detailed how to "time" your charging to let you wear the watch nearly 24/7. I gave it a try for a few weeks, but I didn't find the benefits worth the hassle.

And, as others have pointed out, that comment of Shiller's was especially out of place given how many Mac users point to their still functional and useful "ancient" Macs.

Or iPads, which Shiller presumably doesn't mention. It turns out that the iPad 2 (released 2011) has the most users and almost twice as many as the next highest model. When was 2011 again? Oh, right, five years ago.

Every device that is capable of running iOS 8 is the iPhone 4S and greater...so pretty much 5 generations of devices. I doubt many people have a 5+ year old iPhone at this point. iPhone 4 and under account for 4% of the current iOS market share. (source: https://david-smith.org/iosver... )

I doubt that they are now using this as a gimmick to try and force people to upgrade to a new handset at this time.

your speculation that it is lower, while interesting, does not equal proof. Your guessing that half of iphone users are on the new version because they bought new devices.. An idea that is completely baseless. And you provide no evidence to support it in any way.

So how about some facts.

Here's a link to a page, from an iOS/Android app developer, showing iOS users upgrading to the latest version. Within 2 weeks, 60%+ are using the very latest version (5.1.0), and 85% are using 5.0.0, 5.0.1, or 5.1.0.
http://david-smith.org/blog/2012/03/10/ios-5-dot-1-upgrade-stats/