I'm sure MS could pull an Apple and take one of those, write a new GUI for it (so that you can't just call it by the old name and run X apps on it) and include an XP VM in under a year. But what would that get them?
In a word: Security. In seven words: Security and a more flexible code base
Having at least enough programming experience to know I'm a lousy programmer, I'm not someone who's going to think it should be rewritten for the sake of being rewritten, I think there are a couple of good reasons for doing so.
The first and foremost among them would be security. That backwards compatibility is often times getting in the way, or at least complicating, the fixing of security issues.
Take IE's ActiveX, which was developed in the age of innocence for the Internet. It could be argued ActiveX made malware possible, but that's another discussion for another time. For our purposes here, we just need to know that Microsoft never really bothered to sandbox it properly, and their idea of security initially was that people would digitally sign controls so that if something went wrong, you knew who to sue for damages. So fast forward a decade or so to today, and we see how well that idea worked out. However, at this point, there's really no way Microsoft could go in and properly secure ActiveX without breaking a significant number of ActiveX controls, which would have who knows how many Fortune 500 companies calling up with rather unpleasant messages about how their company Intranet, last updated when IE4 was the latest and greatest, suddenly stopped working.
Beyond that, anyone who has enough programming experience knows that if a program goes on for a long enough period of time, it will invariably develop in ways you could never have anticipated when you started. So there will ultimately come a time where trying to shoehorn and massage your existing code into the new directions will ultimately hamper progress, lead to more bugs, etc. Plus, along the way you develop experience about what things worked really well, which ideas were dead ends, etc. When Windows was created, it was more or less at the height of the individual PC. Every computer was an island unto itself, and if there was any networking going on at all, it was via tightly controlled corporate networks. For the most part, there was no Internet, so no need to worry about external intrusion to the network either. Windows was designed with a single user in mind, and then giving that user more or less free reign over the entire computer. That holds true, to a somewhat lesser extent, even with NT. Times have changed, and those assumptions really don't hold true anymore.
Microsoft could, potentially, create a fully multi-user OS, that has a strong emphasis on the multimedia demands of people today, while being able to also take the time to design those features in a more security conscious way. For years Microsoft put features first and security was sort of an if they got around to it second. So here's an opportunity to build an OS where they can take their time and consider the security implications of various features.
So what it could help Microsoft do is avoid another Vista, where they had a number of grand ambitions that they had to scrap one by one because of the need to maintain that backwards compatibility. They would have a much more flexible foundation to build on. I'm betting if they did something like this, it'd blow Mac OS X out of the water, just like Mac OS X blew XP out of the water, and probably put Linux on the desktop back even further.
And, as already covered, with there being hardware level virtualization support, the transition could be done with a considerable level more grace than Apple was able to achieve when they moved to Mac OS X. The only real risk would be that people just keep writing Win32 apps instead of WinX (or whatever they call the new API) apps. So there would have to be some method in place to discourage people from that, and Microsoft would have to actually stick to it despite the pressure they'd undoubtedly get from companies caught with their pants around their ankles for the Y2K debacle. Otherwise they'd be stuck supporting two different operating systems for decades.
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