The history of the correct steps for the Microsoft operating systems for the PC (in my opinion) goes

DOS->Windows 95->Windows 98->Windows 2000->Windows 7

All the other steps like ME, Vista, 8 are all wild mis-steps which are best forgotten (in my humble opinion of course). But from this list you can chart a history of progress from the early command-line days, through a mixed-mode of command line and windowing system through to the GUI-first methodology of the post-2000 era.

This is how it feels Linux has proceeded. The early Slackwares of the early 1990's felt very much like DOS.. Primarily command-line, with a janky (X11) windowing system built on top of it. Most configuration was done by editing config files, things crashed all the time and software support was.. spotty..

Then the Redhats came on board, and IBM took an interest... And suddenly we had "Linux: Phase 2"... We had properly backed distros with actual support. IBM, and later Canonical, put a lot of work into making the windowing system feel better, the configuration madness feel more controlled, and now hardware vendors started to take a little more notice and created actual drivers for the system. Mostly, the drivers were because Linux was being used a server, sharing things like modems and printers, so it was beneficial to do it for office environments. But the advent of the "SOHO" meant that anyone could have, say, an HP Laserjet on their desk.. and thanks to IBM and HP, they could now use their printer on Linux..

But even in the late 1990s, Linux was still a bit of a config hell. Recompiling kernels, failing dependencies, and cryptic error messages just turned people away in droves. But, so long as you stayed on the straight and narrow, email, web browsing, etc, Linux was pretty solid... I'd say by the late 1990s, Linux had entered its "Windows 95" phase. It was good, and was gaining traction, but was still very wobbly and prone to hard crashes and weird driver problems.

In my humble opinion, progress on Linux felt like it stalled from about 2000 to 2010. It was a period of consolidation. While the number of distros exploded, they were all just variants on the same theme. Some offered more bleeding edge releases (with all the wobbliness that that entailed), while some were more stable. Plugging away in the background, Redhat, Debian, and the other main distros, just kept the candle burning, gradually and slowly improving while all these other little community-made distros rose and fell.

If, like me, you were a debian user, the 2000s felt very solid. Debian just kept getting better and better. Support was growing for more devices, it was available for more things, and each release just felt more solid. There didn't feel like there were any major breakthroughs unitl Ubuntu became popular towards the middle-to-end of the 2000s.... Ubuntu really did feel like the "Windows 98" era had begun. The UI was clunky and slow, but felt solid. It was clearly no contender for the "best UI" award, but it worked, and Canonical did some good work in standardising things. As a debian user I tried Ubuntu a few times, but bounced off the lack of software support.

But it's felt like we've been revving our engines ever since. It just doesn't feel like we've emerged from the history of needing to edit config files, of having to side-load random patches to fix little issues.. it's getting less and less necessary, but we're still not free of the command line. It's a shame because, unlike Windows 98, we already have a proper 64-bit pre-emptive multitasking core. We need to make that final break from the command line and having to hand-edit the config files in /etc to make changes to things.

Windows took the approach of moving all that crap into the Registry and providing users with "regedit". That's what Linux needs to cut out a major percentage of the command-line wrangling that people may still need to do. Couple that with the Service management application rather than "systemctl start..." on the command line, and I feel we'll have emerged fully into the Windows 2000 era. Until then, for me, this feels like we're stuck in the command-line Windows 98 era, and people are still wary of Linux for it.