Getting video editing software to work and stay working. I gave up; I work two jobs and have limited time anyway.

Bonuses: some gaming stuff doesn't work well, and a bunch of HAM radio stuff has huge audio headaches (if it builds and runs on the machine without endless tinkering and hunting now-outdated libs).

I do have a laptop with linux that basically never gets touched anymore (mostly was using it for HAM stuff). I used to dual-boot on this machine but, with no video editing and WiresX and such only supporting windows, it didn't make sense to keep switching. I've been using linux in varying capacities since the late '90s and loved running gentoo building everything up back in the early 2000s. I still use it in varying capacities at work, but I can't daily-drive it on my main machine.