Not a diehard Windows user here (I wouldn't have said). I've used quite a few Linux distros over the years and of course all my servers run Linux; I'm quite comfortable with the CLI - that's where I started with the BBC Micro!
But Linux desktop? Half the software (hyperbole check) I use is available only on Windows so it's either spend ages finding an equivalent and losing years of familiarity or use some gruesome kludge like WINE. Been there - and the hoops you have to jump through are many and not all issues are resolvable.
Life's too short: an OS is about support for the apps, not the OS itself; I don't spend ages interacting with the OS but with apps. Yes, Windows does force some horrid choices on you, like the M$ = Disney approach to the UI, like it's single-user only lockdown, and like its licensing.
I should add that the years I spent faffing with GEM, DESQview, OS/2 and even NeXTstep are not included in my mental map of what really happened back then... :)