When I was a teenager (around early 2000s) I had Compaq Presario CDS-520 equipped with an AMD 486 SX-2 66 MHz. The computer was struggling to play MP3 files at the lowest possibly quality because of the fact that CPU hadn't been equipped with FPU unit.
The operating system was Windows 95. It had it's problems, but it worked. Many of the problems came because of the "DOS" based OS (although the PC was not fast enough to handle NT). Then I had another computer with Pentium 166 MMX paired with Windows 98 SE. This time the computer had much more power, but still, crappy Windows "dos based". It crashed every hour, that was a nightmare. Especially when you've loaded the computer with some software.
And the need for reinstalling OS after couple months because of the viruses, unused files and so on. Lot's of mess.
After many many years I felt that nostalgia and installed Windows 98 on one of my computers. Don't know why, but it felt like almost unusable piece of crap. You want to copy files from CD-ROM? Bang, you got freeze until copying is done. You want to put more memory? Nope. It will crash your system spectacularly. And so on and so on.
Maybe my expectations were too high, but after that experience I'm cured and I don't have "DOS" based Windows on almost any of my computers.
Since then I'm always trying to put Windows 2000 whenever is possible. I found it to be rock solid, stable. It handles dual core processors well, it handles let's say 2048 MB of ram with no issue. Also developing programs for the NT platform is a lot better experience (Windows 2000 is compatible with Visual C++ 2005 and MSVS2005 IDE).
Since then I'm trying to stick with NT based OS'es from Microsoft. Mainly Windows 2000 Professional and Windows XP. I hope some day I will give another try and put some 9x OS again on my PC. This time with a lot lower expectations 😁
PC1: Highscreen => FIC PA-2005, 64 MB EDO RAM, Pentium MMX 200, S3 Virge + Voodoo 2 8 MB
PC2: AOpen => GA-586SG, 512 MB SDRAM, AMD K6-2 400 MHz, Geforce 2 MX 400