As seemingly one of the older guys on HN these days, I went through this kind of frustration several times already with Microsoft.

In the late 80s / early 90s Windows was, in my personal opinion, one of the worst UIs. It wasn't even a proper OS. Nearly every other personal computer shipped a better windowing system. But IBM-compatible PCs were dominant so whichever windowing system monopolised on that was going to be dominant regardless of their quality. This made me grumpy.

But then Windows 95 came along and it was actually pretty impressive. I liked Windows 95 - for a bit. However it didn't take long for the 9x to show it's warts and instead of fixing the constant stream of kernel panics, fixing their reliance on DOS bootloaders, or even just adding desperately needed power user tools (many power users like myself ended up writing our own utilities to get around Windows 9x's short comings) Microsoft just kept bundling new features; forcing the system requirements to jump significantly with each new iteration for seemingly no real functional benefit. Windows ME was easily the worst of all Microsoft's OS (it made Vista look usable in comparison).

But thankfully there was an alternative to the Windows 9x line, and to ME specifically. Microsoft had done some serious investment into their NT line and released Windows 2000. Hooray as because they added so many much needed usability little tweaks: shortcuts to Notepad (back then people still actually used Notepad) so no more clicking File->Save for quick edits. Windows 2000 was also rock solid compared to the Windows 9x range. In fact the only times I've managed to BSOD Windows 2000 was when playing around with undocumented APIs - so pretty much my own fault.

Windows 2000 also looked doubly good because around that time Mac users were stuck on OS 9 (albeit OS X was released shortly after). Mac OS 9 was just as poor as Windows 9x in terms of the frequency one would need to reinstall. Linux was obviously around at that time but we're talking before the time when people even joked about "this year will be the year of the Linux desktop". Linux was usable but a long way from being a recommendable desktop solution for those who want something to "just work". There was another option back then though: BeOS. Sadly by the time of Windows 2000 BeOS was in it's twilight years. Struggling to gain any traction and suffering from the blow of Apple buying up Next (and Jobs). I still used BeOS 5 a fair bit around that time though but more for fun than for productivity as Windows 2000 had better software support, better development tools, etc.

This was when I started to forgive Microsoft for releasing such substandard software in the 80s and 90s. It didn't last long though. XP was twice as resource hungry, twice as ugly and -upon it's initial release- offers nothing of benefit to 2000 aside quickly booting times. XP obviously branched off significantly with each new service pack but it was too late because I held onto 2000 for a long while and then by the time XP really evolved into a new entity, desktop Linux was already good enough that I'd migrated to it as my main OS (only using Windows for specialised "pro" tools). Then with the release of Vista I ditched Microsoft entirely. To be honest I'm glad I did because with each new release of Windows it's felt like control has been inched away from the power user in favour of dumbing things down for the tech-illiterate home users.

As someone who spent their entire career OS-hopping with no real alliance it was painfully obviously how Microsoft was hurting competition. But I guess that's what you do when you're on top. If you're an underdog then you fight for market share by being better at particular things - lots of things if needed. But when you're at the top it's all about retaining market share - so you focus on keeping people on your platform. A priority which doesn't necessarily fall in line with being technically the "best". However the internet has dislodged the importance of the OS. In many ways the browser is now the kernel. Sure many people -myself included- still prefer native applications but the rise of web apps has done more to aid Linux adoption than anything any single company has contributed (Canonical included). Bill Gates could see this coming though. Hence why he tried to dominate the webspace with Internet Explorer and platform specific web controls like ActiveX and it's predecessors. He did a pretty good job too - for a while.

I actually don't hate Windows 10. I have it on a spare work laptop as an emergency in case I manage to foobar my other Linux machines (I run Arch, so it's not too difficult to break if I'm feeling careless - but usually equally easy to fix as well). WSL is a nice feature, miles better than Cygwin ever was. The cmd terminal finally has some much needed usability tweaks. Overall it reminds me of the subtle usability improvements Windows 2000 pushed that made me warm to Windows nearly 2 decades ago. But I'm happy with Linux - it functions the way I personally find the most productive and, frankly, I doubt I would ever trust Microsoft as my primary platform again anyway. However it is amusing to watch new power users go through the same highs and lows with Microsoft as I had done in the 90s. It's just another one of those cyclic trends I've observed in IT (along with technology being discovered and reinvented)