For me, the big change came with Windows 2000. It had user benefits from 9x in a stable package. That was the first version that I can play games on and also leave it running for months, just like a Linux box.
They would have to put up with Windows ME, at least in Microsoft's eyes. Which was the first version you could play games on and leave it running for hours between crashes, lol.
I also used Win 2k Pro and it was an amazing leap coming from 98, yes. My laptop came with ME but it sucked so bad I changed it after a week.
It depended on the definition of "hours" but sometimes the "hours" were very short.
Yes, you read that right: DirectX 3.0a.
Windows 2000 by contrast supported DirectX all the way through DirectX 9.0c, same as Windows XP, 98, and ME.
This is why Windows 2000 could run games properly.
Win2k was a huge improvement in every respect. My 2c.
(1) Win2k Home was much cheaper than Win2k Pro. Possibly an upgrade version was cheaper still.
(2) I had a bootleg version
(3) I started working for real money in 1999 so didn't care that much
(4) An OEM CD came with the computer hardware kit.
https://www.cnet.com/tech/tech-industry/microsoft-outlines-w...
> When it debuts in February, Windows 2000 Professional will sell for an estimated retail price of $319, the same as its predecessor, Windows NT 4 Workstation.
Note that there was no "home" edition of Windows 2000. https://en.wikipedia.org/wiki/Windows_2000
So it's one of 2, 3, or 4.
Another option was student bookstore. Microsoft sold its wares at universities at steep discounts.
Edit: a sister comment jogged my memory. I bet it was either a giveaway by an EECS dept or a heavily discounted disc from the university bookstore. Which is why I do not remember paying a noticeable sum for it.
I still wonder how they would have thought this was better in any kind of way. A windows 2000 home release could not possibly have had as many problems as ME.
When Windows XP came out, Microsoft unfortunately made them report every key given out, and the free ride was over.