I'm in my Mid-40's, I've been in the computer biz since around '86 or so, with computer experience dating back to the late 70's.
When Windows 2000 came out, I had just finished getting my MCSE on Windows NT 4; at first I wasn't too impressed, they did a lot of things differently for no apparent reason, and the new features didn't seem like they were really worthwhile. But it grew on me... a lot. by the time SP4 came out, I was fully and totally in the Win2k camp; it was the greatest operating system on the planet, I even stopped thinking so much of how better OS/2 would have been if IBM wasn't so freaking stupid.
About this same time, I noticed a shift in the way Microsoft was doing things; they started getting really weird. before this period, you could go to the Microsoft website and be fairly certain of finding something neat somewhere that you could download and play with that might help you do a task, or just have fun with; they changed to having very narrow options for things, it actually became hard to find the few things that still existed, they seemed to be hiding the neat stuff from everyone except targeted communities.
Then Windows XP came out. Integrated DRM. phone home registration. thread limiting. all sorts of steps backwards in what the OS would let you do in comparison to Win2k.
Totally inferior as a platform to Win2k, except in appearance. not even as stable as Win98SE was, until SP2.
Of course, it was immensely popular, being as how it shipped on every new computer. I was still pretty happy, as there was absolutely NOTHING that XP could do as a platform better than Win2k, so I wasn't forced to use it. After SP2, WinXP pro made a decent workstation client, so I didn't judge my clients too harshly of they asked for it, they just didn't know any better, and there was no reason to get into a pissing match about it.
Windows 2003 server came out. it wasn't bad, but it still didn't provide the features of Win2k; a server platform that uses resources for prettiness and doesn't add anything to the mix, with a few evolutionary improvements that were frankly "blah"; I didn't really discourage my customers from using it, unless they were talking about "upgrading" a win2k machine, of course.
Then came Vista. Evil. I refused jobs and clients if they insisted on working with it; a lot of my contracts involve heightened security situations, and Vista will never be wholly the customers, it sold it's soul to the RIAA, Microsoft and whoever has the right credentials supplied by Microsoft.
Then came Windows 2008.
Something must have happened at microsoft. I don't have the source code or anything like that, but I've done extensive testing; it doesn't do anything you don't ask it to. it doesn't have to talk to Microsoft or apparently anyone else. it's pretty damn secure out of the box.
In other words, it's not apparently Evil. I may, just possibly, start suggesting upgrading to it from Win2k installations after I've tested it for a few more months, if a customer seems intent on "upgrading".
If Debian doesn't make more sense, of course.