I don't know whay anyone would use an old Windows system anywhere.
The time i "had" to use Windows was with DOS 4.01 (i think) and Windows 3.11. It was sometimes a pain. Memory issues were rampant.
This was the time many people switched from their homecomputers to the so called standard Windows.
One thing that was nice, was that there was a demo scene on Windows machines. Demos meaning artistic demonstrations of graphic and sound. One of the things that puzzled me that this was not happening on a Mac since this was an artistic machine.
Windows 98SE was good but i remember to see a lot of times BSOD. The first real version that was actually really good was XP and before that i assume 3.11.
Today one has only 3 choices which is either Windows, OSX or Linux. Since OSX requires you to buy a Mac the initial cost is a big barrier for many. This was always the case. Even the first iMac was not that cheap and you had to feel good about to have a actually small monitor.
I always thought that Windows came closer to, in my case, Amiga'ish feeling with a computer. Most software i knew ran on it. And most importantly, you were in control of the system and were able to customize your own hardware a thing that is not really possible with a Mac. Not sure today but in the early days you were able to switch maybe the graphicscard and/or the cpu or at least add another cpu on top of the old one with a board.
Linux on the other hand was great. Open system that gives you all the power you ever need. Problem for me was that not many games (i am a gamer) ran on linux or with either sacrifices or not at all.
And i am not that nerd that sits for days on the computer to figure it out.
That changed today somewhat especially that Steam is available on Linux.
Still, Linux lagged some programs like newsgroups software (i am done with that now) but at that time that was a bummer. There were only a handful available and these had not all the features you could get on Windows.
Not a biggie for others, for me it was. I felt that linux was catching up softwarewise at the time i used it. Today i still have the problem with my webcam which surprisingly doesn't work if i install for example ubuntu.
Anyway, i still think that using an outdated system is questionable. I did like MSDOS 5 but i am not sure if i could connect even to the internet with that. And i do plan to run at one point Windows 8.
I know there are many critics out there but i don't care.