Bill Gates was an asshole from the start. Happy to use freely available stuff from the early computing community as well as using his school's resources to build either DOS or BASIC and then acting like he had built it all with his own resources when ranting about free software. To be clear, I don't gaf about using free resources to build something and make money from it, but his hypocrisy and anti-competitive BS makes that aspect worse with him.

So it was always shit, it was just that once upon a time, they actually had to make good software that ran on very limited hardware in addition to their anti-competitive BS, and then had a period where they kept trying to make good software but didn't realize yet that they didn't need to (like windows ME was pretty much universally panned, but it didn't drive people away from windows in general).

I think it was win 10 that I first felt like I was in conflict with my OS. Like in win 7, I'd spend time looking at each update's kdb entry to decide if I wanted it (and skipped the nagware ones about win 10 entirely, for example). In win 10, I had to jump through hoops just to be able to control when it applied updates on my own timeline, not MS'. Win 10 was the worst for resetting settings, like I get it set up like I prefer it to be, then a few updates later I'd have to do some of them again. Though tbf, I don't recall that happening in the last few years, but other worse enshitification has settled in since then and now windows never even touched my current main machine.