There's a lot of people in comments defending macOS saying that the difference in switching between operating systems will lead to a bad experience no matter what and people just need to power through and learn the new system. I'll say that I've used Windows and macOS both personally and professionally for two decades now (longer for Windows). I'd consider myself a power user in both OSes, I know the keyboard shortcu…
I've had slightly better luck getting monitors to work at all on Windows... by a single monitor. I mean more around system behavior when I plug in a monitor. OSX acts... normal? Stuff moves where I last moved it in that setup, or stays wherever it is. Everything stays about the same physical size. Display-rearranging is easy and perfectly reliable. On Windows, literally anything is possible, often including windows completely disappearing or going completely out of the bounds of any screen.
That said, I have no idea why monitor support is so buggy anywhere. It seems nuts. Is it actually that hard? I get that there are some scenarios where there are no perfect choices (e.g. what do you do with desktop icons / window positions when changing sizes? they've gotta go somewhere)... but the amount of times Windows has shoved windows completely off-screen and made them inaccessible is totally inexcusable. It even does that when going from a small screen to a large one, or just adding a second monitor. What kind of code leads to that??