It wasn't really a matter of familiarity. I've been using Windows since 3.1 and while I've been using mostly macOS since the Vista days, I've always had a Windows machine for gaming.
I was really surprised the problem for me was the Windows ecosystem.
Outside of the major players (Microsoft, Adobe, etc) most of the stuff you find are ugly Win32 apps that look straight from Windows 95, do not support scaling, etc. At the time even the Creative Cloud app from Adobe didn't support scaling and looked super small on a 4K display. Heck, even Photoshop didn't support Windows scaling, you only had a setting to change the UI size from 100% to 150% or something like that.
The other problem is that I couldn't find good replacements for my most used productivity/utility apps. For example Alfred, Karabiner, BetterTouchTool, or iStatMenus. There are some alternatives that solve some of the problems these apps solve, but none that are even half as good. A colleague which is 100% Windows told me that much like Android, Windows users are less likely to pay for quality software.
I also had a ton of hardware problems with the Surface Book 1 I bought and returned to Amazon.
The Mac hardware situation is a real problem though, that is certain. Hopefully Apple has already realized this and is slowly correcting course.