I think your posting is very well stated. (which is basically what I say below, with observations)
I had good reason to move from Windows NT 4 to Windows 2000 back then...Windows 2000 really came with some features I wanted to have, such as fully integrated plug-n-play support and the ability to service the operating system *once* per service pack! (Anybody remember updating NT after installing a new driver or OS feature and then having to reinstall the last service pack? I don't miss those days at all.) Microsoft didn't really have to work too hard to sell me on those benefits.
On my systems, and across a lot of different installations, Windows 2000 proved itself to be a stable and FAST workhorse of an operating system, much more so than any release of Windows had ever been (again, in my experience). It was a bit on the hungry side for RAM and not all that secure. At least the security improved somewhat over time (though I would have like to seen the security boosting features of XP SP2 brought to Win2k).
I moved some systems to Windows XP when some of the software I wanted to use demanded it. Windows XP was definitely slower, naggier (do you want to clean up your desktop? no. how about now? no. now, maybe? no. What about cleaning your desktop...>BLAM!< ... "Local Area Network Connection is now connected, 100.0 mbps...siiiiiigh...) and came with some definite non-features such as product activation, the start of the DRM-related protected output path(s) and other stuff. Oh, and the Explorer windows that lose their shape and size settings any time you change your screen resolution--plus, some, like the floppy drive window, don't save their settings at all, choosing instead to default to some asinine large window that takes over too much of the screen. Yay for progress.
I have no use at all for Vista and Win7, the shell in each one is so badly broken and stripped of capabilities that I came to know and use that I just can't do it. If they were going to copy the Macintosh, couldn't they at least have done it *properly*?
Microsoft won't sell me another copy of Windows because there is nothing I want to be found. Make the damn thing work, make the UI sensible and make it lean 'n' mean...and I'll buy it. Otherwise, no sale.
Windows 2000 still soldiers on with most of my computers. It does what I want and has every feature I need. I'll run it until I can no longer do so. And when I can't, it looks like I'll be done with Windows. I don't know for sure where I'm going yet. Probably a mix of Mac OS, Linux and some type of FreeBSD derivative.
Back to your regularly scheduled programming.