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Depends what you use, we used to use Sai2 and while it runs in Linux perfectly fine with Wine or WinBoat, its file system is so complicated getting around it’s not worth the hassle. And our cracked Premiere Pro didn’t work on Linux either for obvious Adobe don’t work on Linux reasons, but honestly we switched to Krita for drawing and Kdenlive for video editing and both alternatives were if not the same, better than what we were using before. So realistically it’s just looking at what you use daily, searching if it’s Linux native, if not works with proton/wine/winboat and if all else find an alternative- there’s so many resources it’s pretty easy ti switch now esp if your a gamer (minus any typical kernel anti cheat BS they pull, shouldn’t play those games anywho) if you’d like feel free to reply software you use a lot and we can suggest alts from what we know.

Ps. Don't stress about the distro, there’s no wrong answer (as long as it’s not unbuntu lmao)

Some Windows exclusive programs can run in Winboat, a special VM which make it look like a normal program running native in Linux. I saw a video a while ago where someone used it for Adobe software and it worked well.
Some games, especially competitive multiplayer, can't run on Linux because the developers restricted it (basically everything with modern kernel level anti cheat).
I personally haven't managed to get Rocksmith (a guitar hero type game where you play with your actual electric guitar) to work, though others have so it's possible. For most other software I found alternatives, but even on Windows I used FOSS software where possible so most of them exist for Linux as well.
If you have an Nvidia card, like me, and use a Wayland based desktop environment you can experience issues. For me sleep / hypernation does not work at all, my pc does not recover from it and I have to cut power through the psu switch.
Overall it went pretty smooth and Cachy's configurations don't need to much tinkering.