I think both Windows and Linux are scary when you want to exactly fits you need.
In using linux I started to know what is a DE, kernel, kernel argument, GRUB, systemd, selinux, etc. and I am the person that want to learn NOTHING about my OS, they just unfortunately pops up during troubleshooting.
So is Windows, device manager, ipconfig, registry table, chocolatey, cmd vs powershell, WSL, and many more. But I would say, if you don't care about bloat and ads, and are willing to make stupid compromises, like copy a email to a notepad, so you can see it while drafting a new email. Windows might breaks slightly less often than linux depending on your hardware. But that doesn't mean Windows don't break, in fact Windows broke just in the first linux challenge video.
For Linus's experiment, I don't really think it is a fair comparison between Linux and Windows. No one is going to learn a OS in a month, and expect to have the ability to not harm themselves, not on Windows not on Linux not on macOS.
But it does serve as a good simulation of a busy Windows enthusiast moving to linux. Personally, I don't think this should be the only criteria to judge the linux eco system, but it is a important criteria, and linux has many things they can improve in this regard (and they are indeed improving).
However, popOS installer for steam breaking DE is a legitimately rare event, and it happens to the most popular tech youtuber is even more rare...