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I ran W2K through most of high school and until like 2009 when Valve finally dropped support for it. It was a great OS fast, rarely crashed, most games would actually run on it. Valve dropping W2K support meant TF2 no longer ran without jumping through a bunch of hoops
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I had windows 2000 on a laptop in the 2008 2010 era. It was already old at the time, but I actually preferred it to XP and certainly vista. You get NT which is nice compared to dos based 95/98/me but you get those tried and true aesthetics, which work well. I’m not sure I’d go back to it now, but it definitely sticks out as the high point of windows in that time period.
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It really wasn't a bad operating system. In fact it kind of blew its (lame) Win9X predecessors out of the water! I ran on Win2000 for years before finally switching to Linux. Of course Microsoft ended up going a different course with its newer "offerings" and I have nothing but pity for those who still have to use their products on a day-to-day basis.
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> It really wasn't a bad operating system

It was a wonderful operating system. It provided consumer desktop essentials (Plug & Play, DirectX 7, ACPI power management, Windows Driver Model (WDM), and support for consumer I/O interfaces like USB and Firewire) alongside a modernized UI, all running atop the NT kernel. I was extremely lucky to receive a free copy of Windows 2000 Pro as a student, because I rode that horse for years.

Then Microsoft added a green start button and dark blue backgrounds and packaged Win2k for home users as Windows XP.

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the drawback for me was the startup time. it really seemed to hang out on the splash screen for quite a while (just as NT4 did, and ofc they were from the same core)
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IIRC, Win2000 would wait for most/all services to complete startup before showing the login UI. XP would allow login as soon as enough of the system was started to support it. The tradeoff is that you might have slow performance from HDD thrashing while everything else finishes starting up.

It's been 20+ years so it's possible I had it wrong then, or remember it wrong now.

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> The tradeoff is that you might have slow performance from HDD thrashing while everything else finishes starting up.

You would often get audio buffer underuns on the startup sound, if enabled, especially if you had auto login.

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No, that's pretty accurate as I recall. Windows 2000 took a bit, but when it was up, it was up. Windows XP would pop you into what appeared to be a functional desktop quickly, but it was still loading in the background, and some things just sort of sat there for awhile. Win2K was much more predictable. When I wasn't on a Mac during my consultant days, it was on Windows 2000, because it was much more stable than the 98 clients.
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Windows 2000 was the first release of NT5. That's what made it 2000.

Windows ME on the other hand...

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[dead]
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I personally think the hypervisor architecture of 9x and its predecessors (starting at Windows/386) was far more interesting and innovative; while Win2k and the NT line are "traditional" OSes, 9x and 3.x are effectively VM hypervisors that have default hardware pass-through. DOS applications had dismal performance on NT, if they even ran at all.
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Win9X wasn't Win2k's ancestor. Win2k was from the house of Windows NT. WinXP was the merger of the two lines.

Probably very few people switched from Windows 98 to Windows 2000. That wasn't considered an upgrade path. That was installing a different operating system.

Technically Windows ME existed, I guess.

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I daily drove it in the 2000s, and loved it. Later I used it for my server VMs due to the small memory footprint and fast remote response. If it supported current applications, I’d still be using it
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If you ran XP and Windows 98SE you got a close interface, even more with classic mode in XP, which was almost the same.
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There are a few APIs from Windows 7 that are great improvements over Win32, such as DirectWrite and Direct2D.
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You can fix Windows7/8/10/11 with Retrobar
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The only thing better is server 2003.
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Dave Cutler created and ran the Windows NT product line through Windows 2000.

Other people ran Windows XP, but Cutler was still in charge of Server 2003 before moving on to special projects like creating 64 bit Windows and Microsoft Azure.

His attitude towards the eradication of known bugs really led to Windows feeling rock solid, with the exception of driver bugs (being the leading cause of blue screens).

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Having had consulting jobs working with Windows servers around 2015, this was ruined for me. Sooo many ancient out of support 2003 severs. Seeing it actually triggers some light anxiety ("oh no not another one!")
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I ran 2003 on my laptop for ages. Only tricky part was installing the audio stack.
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