I started read this article about Windows XP just to fill time, but by the time I got to the second page, I was noticing some subtle and poignant things being said.

The initial simplicity [of Windows XP] almost never survives contact with software installers. Most of them ignore Microsoft’s programming guidelines by dumping shortcuts and icons across the Start Menu, the desktop and the “tray,” that parking lot of tiny icons at the bottom-right corner. Good luck finding anything on the screen after you’ve let the likes of AOL Instant Messenger or RealPlayer have their way with XP.
With all that extra software, Microsoft needs to persuade other companies to play by its rules, but it’s had trouble getting even its own programmers to do that. The mere presence of Windows Vista can’t change this failure to communicate.

From device drivers to installed software, it all basically does whatever it wants to do, due to Microsoft’s approach to system architecture. I am fully convinced that Windows is a product of consumer usability, and not of any intelligent security design or means to be solid and stable and loved for decades. Now, whether that is good or bad is another story, as Microsoft has grown rich and huge for those choices.

The operating system has done little to ensure that programs move in and move out in an orderly manner; they can throw supporting files and data all over the hard drive, then leave the junk behind when software is uninstalled. As a result, something that should have been fixed in Win 95 — the way Windows slowly chokes on the leftovers of old programs — remains a problem.

This is all too true, but again, what alternative is there? And with moving forward in Vista, how exactly will that fix everything? So many programs are bound to act funky or outright break with the new OS. People who have paid for these programs will clamor for support with upgrades (which thankfully software vendors have gotten consumers used to purchasing these upgrades). But, in the end, turning this huge ship that is a Windows-based community around is not going to be easy, or maybe even possible with the Windows OS architecture.
Imagine having Windows running so many important things for years, or even 20 years from now. The world is also becoming more PC-literate, but you can bet that 99% of all the next generation users are growing up with Windows, as opposed to other OS flavors, although I will give that next-gens will be better able to adapt to other OS options if they so chose to. This means that there is a very real threat to *nix servers and tools that they will slowly be bred out of existence (of note, putting *nix into the hands of developing countries can then be both a saving grace or also further stratification…).
Hopefully Windows gets some things right with Vista, but somehow I really doubt it. XP was a major step for Microsoft and it has lasted 5 years during the stabilization of the PC in our daily lives, young and old. I think it will look prettier, be larger, be more complex, will have more layers and layers of cool graphics and security apps, but it all just covers the same buggy and outdated architecture underneath.
At least it still means job security. 🙂