Incredible that companies like Apple (Mac), Atari (ST) and Commodore (Amiga) weren't able to fully capitalise on their leading position in GUI based OSes of the time, which were miles ahead of both MS and IBM.
The internals of pre OS X Mac OS are horrific and disturbing. They are in no way superior to the internals of Windows 95 and are at best only perceived superior due to a different user experience peppered with a healthy dose of self-delusion, certainly not through stability or performance. They are infantile compared to OS/2. Moreover, over the next few years after Windows 95 was released the PC improved greatly while the Mac mostly stagnated. Around the Power Mac era things were roughly even in terms of capabilities and performance though the Mac was significantly more expensive, by the Pentium and especially Pentium II era the PC began to become objectively more powerful than the Mac.
This put Apple into a freefall that they were only rescued from by the return of Steve Jobs who established style as a foundation the company rested on and pushed them into digital media and mobile devices, as well as forcing a hardware architecture migration (to the formerly hated x86 from the PowerPC architecture developed by a consortium of which Apple was a huge part of) and a complete OS rewrite (transforming Mac OS from an antiquated bucket of kludges into NeXTSTEP in Apple clothing).
At the time in question though Apple was pushing old, slow hardware at a price premium in a market that was rapidly passing them by.
As for Windows vs. OS/2 it's at best complicated. It's a bit like a micro-cosm of the PC vs mainframe debate. The raison d'etre of Windows 95 was backward compatability with a low memory footprint.
That may seem like a small thing, or at best not a thing to make so many enormous compromises over, but back then it was everything. The problem with doing multi-tasking "right" was that it imposed a ~4mb RAM requirement per 16-bit application being run at the same time. That is nothing today but back then 4mb was the minimum requirement for installing Windows 95, and it represented a cost of around $100 in 1995. Owning a computer powerful enough to run even a handful of 16-bit apps while running OS/2 or NT was simply above the economic means of a lot of people. And by the time technology caught up and RAM became cheap enough to make proper multi-tasking cost effective there was too much Windows 9x network effect for competitors to make much headway.
That experience ranked up there with writing my own PPP init scripts and endless hours tweaking my fvwmrc. I didn't play video games during that period, because I was quite seriously having more fun learning every nook and cranny of any unix or unix-like system I could get my hands on.
And then folks complain today about the tiniest things!
Back then we all thought "computers" was a hardware game. Only Microsoft realised the hardware didn't matter, software was the main game. And yes, I realise we have swung back to the "integrated hardware/software platform" thing being important again. Picking winning strategies in platform wars is hard.
Yes. This was one of Bill Gates' many strokes of genius. After just one year of Traf'o'Data (Microsoft's precursor), Gates saw that the future was in software, not hardware, and he created Microsoft centered around this very vision (while Apple bet the farm on hardware).
The clones did expand the Mac market, but Apple was so incompetent at that point that it didn't know how to handle that.
And the thing that probably saved Apple in the late 80s was the desktop publishing business.
I know that is the conventional story (and pretty similar for the Amiga). I'm not convinced.
I think that both the Amiga & the Atari ST were too far ahead of their time. They were multimedia workstations, without anywhere to play that multimedia (except on other Ataris and Amigas).
Like you said, the Mac managed to hit the desktop publishing wave, which was exactly right for the the paper-centric late 80's and early 90's.
I never used things like MiNT, but those weren't supported by Atari anyway.
Atari just didn't have the resources to sink into an OS that could compete. They knew how to make cheap hardware, but after a while the PC ate their lunch. Nobody wanted to do biz with the Tramiels, so games were pretty much off the table.
...and education, and government, and academia. Apple was a pretty safe bet in the 80s (The Mac IIfx was designed to government specs and was the fastest desktop PC around). They only really started to lose market after Windows 95.
All I recall from childhood/teen years is "IBM compatible PC" a mantra on every TV commercial IBM or others produced.
A PC was for business and you were rich or a fool to spend thousands on something so useless to a regular Joe.
Apple was even more expensive and even less common than a PC and even so Apple was quirky and drew pictures, ATARI and Commodore were for games.
They were in totally different worlds. Back then I wouldn't have even thought to have one computer that did everything.
If there was any stigma, it was for being on the opposite end of the spectrum -- having a computer whose primary selling point was that it was cheap, like a Commodore 64. The C64 was a fine machine for the price, but nobody was going to ooooh and aaah over it they way they would if you took them into your Dad's study and showed them MacPaint.
I was the only one, among my circle of friends owning computers, that had a PC instead of an Amiga.
My dad thought the Amiga were only good for playing games, for anyone serious about computers, PC was the way to go.
So I was left reading 68000 Assembly manuals, some Amiga reference books, and playing with them on computer parties we used to organize.
In any case, the only way to buy any of them in my home country was on credit.