It kinda is Microsoft's fault. If Windows updates had better software compatibility between versions, it wouldn't break so many business apps.
Ever since Windows 95, I always wished that Microsoft would overhaul Windows and make it more like iOS (with sandboxed apps that are installed / removed / updated / reset like objects). There should be a legacy compatibility environment done the same way Apple kept OS9 support for a while after OSX.
WHAT?
1) I used to have to do a plethora of admin stuff for a smaller company (actually, the company was quite large, but our sub company of the parent company was quite a bit smaller (700 workstations, 50-60 servers) with a LOT of legacy/old applications. In my 7 years of being there, I can't recall many times where a Microsoft update broke one of our apps, and we had to go through and pull said update. The only things that come to mind are vendors refusing to support Internet Explorer 7, 8, 9, or 10. There was one vendor that 'forced' us to keep IE6 around for a LONG time.
2) Even if an update did break an app, generally what that means is the application was using a "flaw" that was corrected with the update. At that point, you pull the update and prod the developer to provide a patch for the app. But I can't recall doing that once.
3) Backwards compatibility is not something that many get right. Java? We had several Java based applications that all required a specific version (down to the sub version) and making two Java apps work for the same system was frequently a PITA. Couple that with the fact that Java by default wants to update itself, and there is a LOT you have to do to keep those apps from breaking. Far more than I have ever seen from anything from Microsoft.
4) As for sandboxing apps, that's not really the issue. The issue is what the application uses to work. Is it Java? Is it Flash? Is it .Net? Is it? You can sandbox an app all you want, but the problem that hits the surface is a shared component of the OS. Sandboxing the app is going to do nothing to prevent app problems if you update Java, unless the developer can build Java into the app installer that is specifically available for the application and not a shared component.
4a) Companies are in charge of what they do with apps. MANY companies are moving their apps to the cloud. At that point, all you have to do is ensure compatibility with whatever browsers you wish to support.
I don't buy this as a MS problem. They're doing what they can to help on their side. Compatibility mode in the new browsers has made supporting legacy sites a breeze.
But for the life of me, his discussion is about a 13 year old operating system, and we're talking about Microsoft moving to fast? Holy crap. I'd say that most people could move to Windows 7 after it's been out a year and realize that it was the one OS that was the "new" XP. The face of most business workstations. I can see the metro-ness being a turnoff in Windows 8, but frankly, the functionality is similar to Windows 7. There is no reason for companies to hold back on updating their workstation platforms for 13 years. 5-7, sure. 13? What dafuq?