Linux

Gonna be real, I haven't had to bother with my OS for the past two months, so I disagree with a lot of this post. The take I disagree with the most is that things that would be difficult regardless of OS are somehow "harder" in Linux though. Getting old games to run on Windows is also a massive PITA, and oftentimes can be easier on Linux since you can always just run a WINE instance using whatever version of Windows the game was originally intended for. Same for old obscure software, anything from like the XP era does not play nice with Windows 11 in my experience. It sounds like the bigger issue is that you have learned a lot about Windows, and haven't learned a lot about Linux, so your knowledge base for Windows is better.

The actual issue I think is huge for your hypothetical "middle user" is hardware based. Some hardware is just better for running high performance applications on Linux than others. In my fancy, shiny, top of the line rig, my experience in getting games to work is I download them and run them with Proton. I've done no troubleshooting, barely use any applications other than Steam for gaming, and so far have not found a game I wanna play that doesn't work. On my old Nvidia-based rig that I replaced, however, it was the exact opposite story. Nothing ever worked, I was constantly looking through error logs and trying to troubleshoot, and most of the time the answer was hardware that wasn't properly supported.