I remember Win2K. It was the first version of Windows that I'd ever worked with which didn't crash the moment you so much as sneezed around it.

I rather liked XP a lot. It combined the power and stability of Win2K and its NT roots with the flexibility and compatibility of Win98.

But then Windows Vista came along, and… dear Lord, what a disaster that was.

From a business perspective, Windows 7 appears to be the last desktop-focused business release that Microsoft will produce, at least for the foreseeable future. This strikes me as a very stupid strategy.

Of course, Billy snatched them up, and built his entire Brand off of the NT architecture. But, as time has gone by, those coders have moved or retired, and windows 8 marked the last hint of NT architecture.
It has been replaced by a 'hot new architecture' which, obviously, suffers from the fact that every coder Microshit is hiring today is a bargain-basement nutsniffer. When you pay coders minimum wage, you get minimum wage coders.

Windows 10 marks the end of Micr0s$ft relevance. Now they are coasting solely on momentum, much like apple. I don't know what OS will rise to push them aside, (Linux cannot compete with a marketing giant and Apple's offering is worse than 10) but I am betting it will be something like 'android for PC'. At any rate, Micr$soft is on it's way down.

Other than that….. Yeah. Win 7 was truly the high point, and refining a bunch of its bugs out, leaving the front end mostly the same , implementing certificate based features management (of, say, wifi) would have been awesome.

But no – we had to have an OS intended – in a half assed manner – for a tablet. Thank god they dialed that back or it would be unusable.

Frankly, MS does everything half assed or total overkill, on the workstation / OS side.

The registry for one, was a reaction to developers leaving configuration options every damn where. So they create one (actually several acting as one, with some parts in the user profile) database that can easily break, and often did.

Or icons. They re-dressed the icons for XP. But the user design was only skin deep, with a number of Control Panel > Admin icons being the same as they were in Win 2000 (and some older than that, effectively)

You redesign and reflow the entire OS, redo all the main user facing iconography, but can't be bothered with a few stragglers? Really?

I've had my issues with linux but the last few years have almost, almost gotten to the point that outside the use cases you mention and a few related Mac-OS or Win-only tools, I'd be able to go Linux only, and NOT spend far too many hours under the hood just getting crap to work. I say this as someone who had a household server that had, at various times, run Suse, Debian, Slack, Centos, and Fedora.

Mostly, for me, it's syncing, contacts, and calendars. I have to use either iOS or Android. Only the latter works with Linux, and one still then gets stuck with…. Google. For all of Apple's sins and whatever you think of their design decisions (or their database object syncing) they were seriously on board with "We have your data, we don't look at it, and design our hardware so other people can't look at it either – see the San Bernandino phone.

THAT said, While Jobs was a flaming liberal, he was focused on product, willingly cannibalizing his own markets instead of resting on laurels. And he considered corporate charity drives and the company officially standing behind causes, or ordering based on gender/whatever, to be a case of losing focus on what mattered.

Tim Cook has begun the convergence, and I see many signs of Apple descending to mediocrity. That said, so many other companies, and various open source projects are either making the same descent (the OS projects that were excellent) – or descending to utterly crappy and buggy.