Photoshop! After over a decade of using it, most of the things I do there became muscle memory and I have absolutely no reason / incentive to learn different software (other than being able to use Linux). Ruining it in Wine proved to be a horrible experience - after a couple days of bruteforcing a setup that started, the graphics performance sucked so bad that it was nearly unusable.

I ran Windows -> Hackintosh for 2yrs (until it exploded after an update) -> Linux for 2yrs (until it exploded because of NVIDIA drivers ruining my stability) -> back to Windows after they released WSL2.