Win 7 was cool to tinker with but buggy as hell to the point Ubuntu was just as much work as the time but with even more possibility.
8 was so bad it was worth skipping.
10 was the peak of it just works for windows. Gone were the days of troubleshooting triple AAA games on my PC, they worked or needed patched by the devs.
That said if I NEEDED something to work choosing windows 10 or server was an exercise is maschocism. Need this container? Unsupported. Need this service configured like this? Gfl finding where that is set. Need HA? Just Ha. Certain network configs beyond basic client? The guys with decades of Windows admin exp still have no idea.
I had to troubleshoot both but windows gives you the nice feeling of being able to say "this sucks they should fix that" because I know ain't. Its not built for me to fix it either. Linux however begs you too. Its all there, you can do anything, even you might not really want to.