Except for video games, all software I use daily is open source and cross platform by now, but when college demanded for me to use Adobe software, I would boot my Win 10 VM. I also boot that VM to test if the software im developing works well on Windows. I also run my Logitech mouse software in a VM with USB passthrough.
Besides games, I think the only Windows program I run with wine is a tool to extract the BGM from the official Touhou games.
Before I had a 3DS, I would use a Windows tool on my VM to decrypt my totally legally acquired ROMs
I have a tendency to use “DIY” systems, basically systems that leave the administration up to me, and either have a minimal base or a customizable, powerful but convenient installer. Then comes the package manager’s strengths and weaknesses, and the package repository and its release cycles.
My favorite OSes of all are:
I never used Gentoo so I don’t classify it, but i believe I would like it a lot if I used it.
And yeah, I have a logo bias lmao. NixOS, FreeBSD and Debian have amazing logos. Something that is neat is when a distro has multiple kernel versions in the repository.