> extremely arcane things I had to fix when setting it up involving host DNS and VPN adapter priority not getting propagated into the VM so networking was completely broken
Are you sure you set up the VPN properly? Messing around with Linux configs is a good way to end up with "somehow" bugs like that.
OSX was a bit janky with docker filesystem slowness, homebrew being the generally recommended package manager despite being awful (why do I sometimes tap a cask and sometimes pour a bottle? Don't tell me; I don't care. Just make it be "install". Also, don't take "install" as a cue to go update all of my other programs with incompatible versions without asking), annoying 1+ second animations that you can't turn off that make it so the only reasonable way to use your computer is to never maximize a window (with no tiling support of course), and completely broken external monitor support (text is completely illegible IIRC), but Windows takes jank to another level.
By contrast, I never encounter the issues people complain about on Linux. Bluetooth works fine. Wifi works fine. nVidia GPUs and games work fine. Containers are easy to use because they're natively part of the OS. I prefer Linux exactly because I stopped enjoying "tinkering" with my computer like 10 years ago, and I want it to just quietly work without drawing attention to itself (and because Windows 8 and the flat themes that followed were hideous and I was never going to downgrade to that from Windows 7).
I also have tailscale running on Windows itself and they don't conflict.
I don't have a need to run multiple OSes though. All of my tools are Linux based, and in companies that don't let people run Linux, the actual tools of the trade are almost all in a Linux VM because it's the only reasonable way to use them, and everything else is cross-platform. The outer OS just creates needless issues so that you now need to be a power user with two operating systems and their weird interactions.