I've once had a Windows update break software, and I was easily able to downgrade the broken update (and it wasn't really MSvs fault entirely, graphics driver issue).
Multiple times I've had ipad updates break apps, and some apps have never worked again because the developers don't bother updating the app, and Apple blocks downgrading because...
I'm not endorsing the stupid stuff that Apple has been doing in the article, but for your case, I don't see what they should have done differently.
Maintaining backwards compatibility for every app is a big technical requirement, and Apple chooses to spend their efforts elsewhere. Microsoft takes the opposite route because they have many enterprise customers who have to keep using an internal CRM that was last updated in 1994 and all the developers have died.
If you want your OS to support abandoned apps, then you should definitely choose Microsoft. But most people have other priorities.
Similarly, keeping devices on old OS versions has a cost too. They could be insecure, opening users to the risk of compromise of their personal data. Newer apps will not work. Having a significant proportion of devices that have not bothered to upgrade stops developers from using the newest OS features (for an extreme version of this phenomena, remember ie6).
Apple prioritizes getting users and apps on the latest OS releases over perpetual support of abandonware. The proportion of users who need to support abandoned software is probably tiny compared to those who can benefit from OS updates. It's a conscious choice, and other vendors choose differently.
I've once had a Windows update break software, and I was easily able to downgrade the broken update (and it wasn't really MSvs fault entirely, graphics driver issue).
Multiple times I've had ipad updates break apps, and some apps have never worked again because the developers don't bother updating the app, and Apple blocks downgrading because...