Most Linux 'reviews' back then were basically a review on how easy (or more likely, hard) it is to install. Most distros installers faired pretty poorly back then. I succeeded in getting RedHat 7 installed, but could never get Slackware or SUSE to successfully install.
So if you're going to start with something like Windows XP service pack 3, meaning that you were someone who didn't jump straight to Vista (I'll be a Vista apologist, but people were being reasonable when they didn't jump from XP), at that point, you're comparing it to Linux distros of 2008. That would be something like Fedora 8, Ubuntu 8, or Debian 4. This was the GNOME 2 era and it was a pretty damn smooth experience.
If you're thinking a bit deeper in terms of user experience for the early, early 2000s, then you would probably put FreeBSD high up on your list rather than treating Linux as an assumption.
It even had a tetris game you could play while waiting for the packages to be copied in the background.
As a kid at the time i installed it on pretty much any PC i could get my hands on - my own, relatives, friends, etc, nobody was safe :-P though they found it interesting anyway since it was chock full of applications and games to play around - and i don't remember ever having issues. I tried it recently in 86box (which emulates old PCs) and it worked as good as i remember.
Though in a way it was probably an exceptional case, IMO that CD was basically the best well-put together distro (especially when you consider that KDE was basically beta software at the time).
I stopped trying to use Linux as a desktop OS since then. But recently I tried for fun installing Ubuntu and everything just worked out of the box.
I still feel Linux is too fragmented, too many package managers, too many UI managers etc...but that's part of the beauty of it I guess.
I remember circa 2004 I set up my non technical brother with one of the earliest versions of Ubuntu, after he kept getting malware on XP, and he didn't have difficulty with it. I was kind of surprised how easy it was. I was a debian and OpenBSD user at the time.
Microsoft wants your money and your loyalty.
I have yet to discover what Linux geeks want except for you to join them in some weird reality distortion field.
Two iMacs. One with Mint and one with Ubuntoo. Both just literally crawl. Alpine is so much faster, and we are gaining speed by hook and crook.
It was dual booting that would get you every time.
By 2002 I managed to get some district installed, but all I accomplished was having my distro eat my lab report (umount? Wtf?).
I didn't really get into Linux until grad school, and then only because i had to use an SGI daily
people want to use windows XP in order to run old software that doesn't run on newer systems. (or because they are nostalgic, but those are not helped with linux, so we can ignore them)
a modern linux distribution is way more likely to run old linux and windows software than a modern windows version.
hence that's why the world needs linux, because it doesn't have the problems that windows upgrades have.
you may argue that new linux distributions don't have old libraries either, which is true, but getting older libraries to install and run is way easier than on windows. and it's possible to put an old linux binary (even one for which there is no source) into an environment and make it workable on a modern linux distribution, and with things like flatpak it is also possible to make such an environment easily installable for a non-technical end user. getting old windows binaries to run is even easier because that's exactly how wine works.
Specifically said prior machines are:
* A Windows 7 Sandy Bridge desktop.
* A Windows XP Pentium 4 Northwood desktop.
* A Windows 98SE Pentium 2 laptop, with a Yamaha XG MIDI sound card.
Microsoft and Windows are downright legendary with their commitment to backwards compatibility, but that becomes even better with access to many versions of Windows and the hardware of their times.
Linux would not satisfy my needs and desires in any of my machines, let alone my daily driver. I don't have the time nor desire to faff around with dependency hell and terminal voodoo and maybe get something that half-works (which will immediately bork to a stiff breeze) when Windows instead will Just Always Work(tm) and get me going.
linux may not satisfy your needs, but not everyone can afford to keep old machines around like you do. and those stories of dependency hell and terminal voodoo are corner cases on linux just as much as they are on windows. especially if someone is going to set up a linux machine specifically to run old windows programs in wine then they most certainly will not run into any such issues.
most cases of dependency hell on linux are likely caused by inexperienced users who follow bad advice to install software from the wrong version or a different distribution. don't do that if you don't know how to do it without causing problems.
I prefer linux in theory for my personal machines but I can hardly get a week without some issue (on ostensibly stable Ubuntu) either causing it to randomly fail when waking from sleep, gnome-desktop having catastrophic bugs like leaking memory to the point where none is left, or pegging the CPU, or stuttering, or....
and even without extensive packages installed I have things breaking there constantly, where I have to fight with apt and etc.
MS backwards compatibility too is really an incredible feat.
They all had GUI interactive installers, and had floppy boot disks to boot (too!)
Mandrake (9.2 is the version I used the most) was very nice, the GUI installer looked very polished, had nice explanations and package selection was done by answering “what are you going to use this computer for?”. A TUI installer was available as a safe option too.
[1] At that time you are in SCO OpenServer territory, SCO UNIX is OLD, but the same applies to OpenServer 5 and 6. It might have been UnixWare (which I only installed once, no memories of it) or maybe SCO Linux (oh, the irony!)