Well, like anything else, each version of Windows (for the most part) has/had its strengths and weaknesses. The problem wasn't so much one of technology (though the tech problems are many), but one of marketing - MS' insistence that each version of Windows could at the time do whatever you wanted and was a panacea for all technological needs was and is just plain wrong. Windows, properly installed, properly maintained, and used by someone who doesn't need a drool-guard for their keyboard can be a reasonable operating system - there are *far* better choices out there in terms of both performance and stability, but if you *have* to use Windows, it can be done in a reasonable manner. It's all a matter of choosing a version and associated software that's appropriate for the computer it'll be running on and the needs the operator of that computer has.
In terms of not-crashing, XP is a close second to Win2000 with SP4, in my experience. I've found that it's more stable and a lot less resource-addicted. However, since support for 2000 has been dropped and SP2 has resolved most of the core problems with XP, XP is the Windows to use if you're going to use Windows - without new patches, XP will very soon out-pace 2000 on the stability count. A good approach seems to be loading XP SP2 and turning off all the XP GUI bells and whistles - get it as close to Win2000's environment and Win95's non-IE shell as possible. The performance improvements are significant, especially on low-resource platforms, and the overall stability is about as good as we can expect from Redmond.
Compared to stuff like Windows Millenium and the OS/2-derived NTs, yes - XP is practically bulletproof by comparison.
On the other hand, 2000 is when Microsoft began pushing "tailored versions" of the same Windows implementation - Win2000 was available in Professional, Server, Advanced Server, and Datacenter distributions. They bowed slightly to the annoyance of the public with XP - available in Home and Professional versions with the server technology re-spun-off as the Windows Server series, but went right back to confounding the public with the half-dozen different versions of Vista and the various flavors of server, maned in such a way where it's unclear which is more powerful / more feature-packed. I thought they finally had a decent model with XP that would have been great for Vista - two versions, one for low-to-midrange systems, one for mid-to-high range systems. Could have avoided a PR fiasco. What I'd like to have seen (and what I was expecting when Vista was announced out of the Longhorn Project) is:
Windows Vista Home: the basic vanilla Vista
Windows Vista Advanced: Vista plus the new 3D GUI and all the other "Ultimate Edition Only" extras
Windows Home Server (coming out soon...): a simple server for things like file-sharing, media streaming, maybe web serving
Windows Advanced Server: a full-bore server, databasing, virtual / shared servers, etc.
Simple. Clean. Efficient. Four possible versions - a simple practical desktop, a sophisticated desktop, a basic server, an industrial server. Doesn't fix the nightmarish problems Vista's flawed technology has caused, but at least people would know what they're getting (and, as I always say, he who buys Redmondware before the first service pack is released deserves what he gets

).
My biggest gripe, though, with how the multiple additions of 2000 and XP were handled is that, within the individual series', they're the same freakin' OS. Take XP Home - that CD is basically identical to the XP Pro CD save for a few instruction files that tell the installation system which files to copy over. Example: XP Pro has built-in backup software, XP Home doesn't. But the installer is on the XP Home CD - you copy the .exe to the desktop, run it, and you have "XP Pro's exclusive" backup package on XP Home, perfectly legally. With a little patience, you can turn XP Home into XP Pro by running a few programs that MICROSOFT PUT ON THE HOME CD (or, more accurately, "didn't bother removing from the XP Pro CD when they crippled it into XP Home").
That means that XP Home is literally a crippled version of XP Pro - only reason this was done was to justify charging more for Pro while "offering" Home as a "less-expensive version for the basic home user" to expand their market-share and mind-share; PR and marketing tactics that have nothing to do with the technology. That's how 2000 and XP were - I don't know if this is true of Vista (as implied above, I'm staying far away from Vista until at least a few months after Do-Over Edition comes out).
Now, in my model, if Vista Home physically doesn't include the non-essential extras that Vista Advanced includes, then yes - you actually *are* paying for more software if you buy Advanced, and you're *getting* more software (as opposed to the same CD with a crippled installer), then MS is justified in charging more for Advanced than for Home. Ditto for the Server versions (assuming of course you're using MSware for anything server related which, as was once put on a.s.r, "is like building a prison out of meringue") - if there's no SQL package anywhere on the Home Server CD, and there is one on the Advanced Server CD, then part of the added cost for Advanced Server would be that SQL package that isn't otherwise available.
But that would be ethical and honest.