I know I'm late to the party, but your statement that Windows has always been an exercise is frustration is most certainly true for you, but not everyone. For me, the last couple of iterations of MacOS before I sold my 15" MBP about a year ago were more of an exercise in frustration than Windows 10 has been.
Yeah, I'd have loved to use Linux as my primary OS but I was limited in what I could accomplish and limited in the hardware I could buy. I had certain things I wanted to accomplish with my new laptop ecosystem and Linux literally didn't have the hardware support at the time to do it. Yeah, it does now... but I would still find Linux intensely limiting due to my use cases today. And quite frankly the hardware support is still lagging far enough behind that it renders itself irrelevant to me pretty quickly.
Privacy concerns? I personally don't care. The metadata collection that Microsoft does is something I don't really give a monkeys about so long as I can get my work done in a simple and effective manner. Yeah, I do some blocking with PFBlocker on my firewall because why the hell not? Just because I don't mind the metadata collection, doesn't mean I'm going to make it easy for Microsoft. And unfortunately that doesn't help when my laptop leaves my house... but that's infrequent enough that I don't care.
I'm not a Microsoft shill, but neither do I care much about the operating system I run any more. I have very little software that's Windows-specific just as I had relatively little software that was Mac specific. I'm more concerned that the hardware I run is capable of working with me and helping me do my work and once I wrote up a list of hardware I wanted in my latest iteration, listed out the capabilities that I wanted and so on neither Mac OS nor Linux were an option for me. Like it or not, leading (or bleeding) edge hardware has never been either Apple's or Linux' strong suits. And there are some people who actually need that hardware.
For the record too, my transition into using Windows 10 was easy, and continues to be easy. My computer is really reliable and has had zero issues even considering I did an upgrade from Windows 8.1 to 10 (8.1 was the OS of choice when I got my current hardware). Usually I'd expect issues but I had surprisingly few. I had to uninstall a couple of pieces of software due to compatibility issues, but I didn't miss them either.