I've tried to switch to Linux a handful of times on my secondary machine, from Vista era up to Windows 11. My primary use case at the beginning was DVR. Couldn't beat Windows Media Center for that in the Vista/Win7 era. Then WMC got the axe so my use case shifted to Plex with other content sources. Tried Linux for that changeover. As an unseasoned Linux toe-dipper, that process was just a bunch of blindly running commands from a setup guide to install everything, usually without an explanation of what each command does. Some stuff wasn't working and I didn't have an idea of how to fix it where to start looking, so I aborted Linux and ran Windows 10. As a largely headless machine (accessible via KVM, but I usually just used remote desktop to manage), Windows 10 updates were a frequent hassle with the full-screen nags for OneDrive and whatnot that interrupted the boot to desktop (and thus prevented my background services from starting), but I lived with it for years, and remoted in when I had to fix something.
This past year, I finally did a fresh start with TrueNAS running all the same apps I was using on Windows. It took a while to figure out permissions, and the process of getting there was messy, but everything is working.
In anticipation of the Valheim 1.0 release, I wanted to setup a dedicated server. I initially tried setting up a spare laptop to run it in Mint, but I ended up reallocating that laptop to my wife so she could dip her toes in Linux. I then shifted to trying to set up a Docker container for it, but had a misunderstanding of where to paste the Docker compose, so I gave up and installed a Mint VM and setup the server inside that VM. Then a couple months passed, and I'd forgotten what installation type I used and also what commands to update/configure, which motivated me to delete the VM and figure out what I was doing wrong with Docker. Got it set up after a little struggle with file paths to a separate storage pool, but it's now working perfectly. Now I have an easy update button in the GUI so I don't have to remember or document any commands. I'd go so far as to say the vanilla dedicated server running as a Docker app inside TrueNAS is a cleaner, easier experience than the default method in Windows. Now I have a friend asking for a server-side mod, so we'll see how that goes...
As for my wife, her main use case is simple Libre Office and web browsing, so there's basically no struggle there. There was one hiccup with her touchpad not working, but she resolved that. She did try to run Clone Hero and ran into an issue with button mapping with her Xbox 360 guitar but didn't have the will to look into it at the time. She'll get around to it.
As for me, I'm a gamer and an engineer. Until all my games and SolidWorks run on Linux, I won't be switching my primary PC off of Windows.