At least Apple gives you the option. Many Android phones either can't be upgraded at all, or aren't on any kind of unified release schedule, so you never know when you're going to be able to upgrade.
The only Android phone analogous to the iPhone is the Nexus line directly from Google, and it's future is far from a sure thing.
If you aren't happy with your release schedule, you can download a custom ROM for your device that implements the new version of Android. I use CyanogenMod 6.1 (Android 2.2) on my G1, which officially is still on 1.6. It's not very bad for me, a bit sluggish but definitely still usable and workable.
Yup, that's what I do. I have an HTC HD2 that shipped with WM6.5 and am running Android 2.2 on it now. Just a few days ago some hackers figured out how to run WP7 on it too.
I know Android supports OTA updates -- which I really love, btw -- but I'm entirely unfamiliar with the custom ROM process. Does it involve anything like "jailbreaking" your device, or are you able to simply install it.
What I'm wondering is if it's something I could have my mom do. That's kind of my litmus test for whether something is a mass-market solution, or if it's something only geeks will do. If it's not a mass-market solution, I'd argue that the chart designer's point still stands. Jailbreaking or rooting your device to support an upgrade cycle isn't exactly a solution for most people.
It does have its issues and is probably not something that you should recommend universally. However, most Moms don't even know when a new version of Android has released unless you tell them, so it's probably not really an issue for them.
The process differs from device to device. Most of the time it will include pretty advanced stuff from the Mom's perspective, things like commandline usage and installation of bootloaders.
That said, it's not very hard for your average Linux user. Just follow the tutorials.
I disagree strongly regarding the Android version issue and moms. My mom, cousins, and co-workers (non-programmer) all seem to upgrade their iPhone iOS without issue. I would expect the same from Android.
Uh, do they all use jailbroken iPhone versions? A standard Android upgrade is easy and great. Rooting your phone and replacing with a custom ROM isn't at "Mom" skill level, just like jailbreaking an iPhone isn't "mom" skill either.
The only Android phone analogous to the iPhone is the Nexus line directly from Google, and it's future is far from a sure thing.