Windows is a very competent OS nowadays, especially if one installs MS PowerToys. AFAIK that set of tools is developed by MS own employees as a side project, and it adds a lot of great functionality (especially Spotlight-like global search dialog that can also find text in Onenote records, something that Windows Indexing no longer does).
I like its simplicity but still functional. Each task can be set as daily or weekly or monthly. It doesn’t limit when the task should be done but we can set multiple notification for one task (this one that keeps me on top). Also, we can set 1 task can be “tick” x times until it is marked as “done”. You can also see how the task is progressing (including our comments) just from icon (to edit, just press & hold down the task icon). We can also set if >3 tasks (or whatever the number) in one page have completed, the task’s icon can be change color to gold, which is very motivating.
Second this. I think, “just work” start deteriorating when their ambition to have major update every year (start around the same time with iOS 7, where all aqua and skeuomorphism design in Mac and iOS started disappear). I personally install (for iPhone/iPad and Mac) one major version old behind to keep my machines “just work” (not always “just work” but still pretty stable).As a late adopter I think you missed out on the golden years (or maybe im just a grouchy 40 year oldbut there was something special about that aqua interface in the early and mid 2000s having come from windows. it was the indescribable finishing touch a builder puts on something that they didnt have to. for example, the slight pulsing [breathing?] of the blue "ok" buttons on dialog boxes. Or the intro videos when setting up a new Mac or a new OS upgrade. I'm sure I am not remembering the times of frustration when software wouldnt work, but back in those days it really did "just work." You should go see the 512 pixels website by Stephen Hackett and look at his Mac OS X gallery that has tons of screenshots from each OS. don’t know about you, but for me it makes me with apple would come out with a macOS Retro edition that is all the stuff of the modern OS but with all the looks of an Aqua OS. Id gladly go back to the days of paying $129 for an OS upgrade if they did that. It was so beautiful and at the time so futuristic looking but in such an elegant way.