Yes, making an OS with pre-emptive multi-tasking with a modern graphical UI that could be installed (and be fast) on an affordable family PC with just 4MB of RAM, is "software mediocrity". The stories of "old glory days" should be reserved strictly to true geniuses who wouldn't touch anything cheaper than 10K UNIX workstations.
I used to work under a CTO who's been in OS/2 kernel group at the time of their cooperation with MS. He's still claiming them all idiots and arrogant pricks, only "their" OS/2 eventually worked out, but "his" OS/2 silently died.
You can't beat at the same time the mighty gorilla (IBM) and ambitious uprising young startup (Apple) on marketing or luck alone, you'd need an engineering arm slightly above mediocre level.
So... I call BS on your comment. I bet Microsoft in the 80s was more exciting place to be than Google is today.
Much of what you're referring to is Microsoft in the 80s, while much of what Chen writes about is from the 90s.
Windows as a platform is an epic achievement in software: they managed to create a commercially successful OS that's pretty stable/usable/responsive even in the face of a combinatorial explosion of possible off-the-shelf hardware configurations.
However, it used to crash all the time and it still has a terrible security model. It wasn't pre-emptive until at least Windows 95, after a decade of work, when a typical PC had much more than 4 MB RAM. The hard work of designing a good, modern GUI was done by PARC and Apple; Microsoft just had to reimplement it for different hardware.
I don't think Windows was good until Windows NT 4/Windows 2000.
Don't act like Microsoft's success is entirely due to engineering, nothing to do with IBM's retarded decisionmaking, nothing to do with Bill Gates's extralegal bullying, and nothing to do with John Sculley's mismanagement of Apple.
Getting back to Raymond Chen, he finds Windows' annoying quirks and flaws to be amusing. He also acts like a condescending jerk a fair amount of the time by disparaging users or developers.
"Windows is a 32-bit extension to a 16-bit graphical shell for an 8-bit operating system originally coded for a 4-bit microprocessor by a 2-bit company that can't stand 1 bit of competition."
