Windows 2000: Like Windows NT, but with a half-baked plug-and-play mechanism to give you false hope that somehow the system would right itself. It rarely did, and most Windows 2000 installations quickly devolved into the kind of blue-screen troubleshooting sessions that were supposed to be a thing of the past. Still, a better-organized setup program -- including some crude hardware autodetection -- helped to shave a couple of hours off the marathon.
Windows XP: An attempt to meld the ease-of-use of Windows 9x with the robustness of the NT kernel, XP was a disaster out of the gate. Many Windows 9x drivers, though theoretically compatible with XP, simply didn't work (NDIS driver support was a notable gray area). And some legacy NT drivers that worked fine under Windows 2000 simply refused to cooperate under XP.
It took nearly a year to shake out the whole hardware compatibility mess, and by then enough new standards and architectures had emerged to ensure that future XP installations would require much patching and tweaking (F6 for the driver floppy disk, anyone?).
Windows Vista: Windows Vista had the potential to be the easiest version of Windows to install ever. And in most respects, it was -- at least up to the point where you actually wanted to use it for something productive. Then it became a waiting game as you listened impatiently for news of Nvidia or ATI releasing yet another prerelease driver for your state-of-the-art video card, the one you paid extra for in anticipation of Vista's Aero goodness.
And then it was install-and-pray time -- pray that, maybe this go-round, the company had gotten it right. That you wouldn't be rewarded for your patience and fortitude by a wonky release, with missing features or -- worse still -- the kind of instabilities that nearly sent you running back to XP with the last prerelease.
Eventually, the mess would get sorted out, with vendors accepting the fact that new technologies, like WDDM, were here to stay. But for a good year and a half after Vista went "gold," creating a stable, working environment was a real challenge. No wonder so many of InfoWorld's readers demanded that Microsoft do something and save Windows XP.
Indeed, it has been a long, rocky road that led me to this point -- a point where I can install a version of Windows and have it successfully recognize the majority of the hardware in my system. A point where, even it if Windows doesn't recognize something funky, Windows Update -- that bastion of false hope in every previous iteration -- will usually find a compatible (if generic) driver. And a point where a visit to my hardware manufacturer's Web site rewards me with a healthy selection of new and updated drivers, all designed to ensure a smooth transition to Windows 7.
It was a long time coming, and perhaps the geeky side of me will miss the visceral challenge of a good old-fashioned, blood-pressure-raising, hair-thinning Windows installation. But the rational side is happy to see things finally improve to a point where Windows just works out of the box -- and where the drama in my life is restricted to the day-to-day struggle of raising two disturbingly tech-savvy pre-teens.