I know a number of iPhone owners for whom upgrading their iPhone 3G to iOS 4 was something they regretted. The performance of iOS 4 on the 3G was piss poor. Upgrades make sense only if they make sense.
[Warning: American perspective here, which I think I share with the original blogger]
That said, I do think that carriers should roll out Android updates sooner, but I disagree with the assertion in the blog post that carriers are in the same business situation as Apple is in. Apple is a hardware manufacturer and wants you to be happy with Apple hardware. Verizon, Sprint, AT&T, and T-Mobile are wireless providers. They know they have you locked into a contract (as most people are) for two years, and a lot of people don't want to switch carriers because it's too much trouble and they want to be grandfathered into an unlimited plan or a lower contract price. The carriers have very little incentive to push software upgrades to phones.
I know people will say "Yeah, but it's really HTC or Motorola or Samsung making the update, not the carrier." Well, then why don't they let you download the update yourself and push it yourself? Why is it still up to the carrier to push? I know a lot of situations in which an upgrade has been officially released but not pushed to all phones. That is up to the carrier. You can't say the carrier isn't the one pushing it, especially since a lot of the bloatware in the Android roms you get on phones is bloatware from the carrier and not the handset manufacturer.
The real problem is that Google made Android "open" to handset manufacturers, and then handset manufacturers and wireless carriers made it closed to users (with the exception of the relatively miniscule number of users who root their phones). Android isn't "open" if you don't have root access (all contract-sold phones) or if you can't uninstall bloatware apps (all contract-sold phones) or if you can't choose to enable software installation from unknown sources (AT&T phones).
I love my current phone (MyTouch 4G) because I rooted it and installed Cyanogen on it. Cyanogen has been an excellent experience and pretty much updated almost immediately. When this phone outlives its usefulness or I'm eligible for an upgrade and just curious about what's new (maybe in two years or so), I'm definitely going for the Nexus line.
I don't mind rooting my phone, but I'd prefer not having to in order to get both a vanilla Android experience and timely software upgrades.