Could be small or big.
My answer has always been that, Linux can't handle everything I'd ask out of it that I normally can with Windows. I know the games issue has been progressing far from the days when that used to have been an archaic flaw with Linux for the longest time. Games might not be the issue except for some concerns I have for some games.
I was taking some time a few moments ago, to check if a program called Firestorm Viewer would work on Linux Mint which could've been my distro of choice. And the description written on the linux page described exactly the kind of concerns I'd have for compatibility and usability from going Windows to Linux.
They said that their viewer was tested and designed to function mostly with Ubuntu and while it could work with other distros, it's not to be expected to be smooth.
That's the kind of sentiment and concern I have always had with Linux if I were to go from Windows to it. There are programs and tools on Windows that I have that are used for specific purposes and I know they will not function on Linux. Furthermore, incase anything breaks down, any and all solutions would only be applicable to that thing that would be far easier to solve than just being SOL if I was on Linux.
It is something as a user that I just can't simply afford to deal with on a regular basis if I made the switch.
So while I may not have too much of an issue running games, I won't have too much of an issue using alternatives, I won't have to deal with the Windows ecosystem .etc I will just be running into other walls that would simply make me second guess my decision and make me regret switching to the point where I would dip back into Windows in a hurry.
I'm aware it's not Linux compatible, I was just wondering on how well it plays with wine, since I heard Photoshop doesn't really like to run under anything (thanks creative cloud).
My issue with Gimp is probably a user issue, as i've been a life-long user of Photoshop until my switch to Affinity (which behaves exactly like Photoshop without the "cloud" BS), although the fact that they only recently got non-destructive effects should probably hint at what I mean (slow development of- to me- essential features). My main issue though is probably just not being used to the workflow.
If Canva, who bought Serif/Affinity last year, ruin Affinity with cloud features, which currently seems very likely, I'll probably try to just deal with Gimp and get used to it.
I don't want to in any way denigrate the hardworking folks who work on WINE, but from personal experience, I have never gotten it to work with anything. I've actually had much better luck with VMs. I believe that WINE itself has a scorecard for how well certain apps behave with it, to wit:
https://appdb.winehq.org/objectManager.php?sClass=application&iId=18332
https://appdb.winehq.org/objectManager.php?sClass=application&iId=20209
Neither of which sounds terribly promising, unfortunately.
You could probably run Affinity on VirtualBox, but that means still having to deal with Windows, and running a resource-intensive program on it that way can be sort of, well, rickety-feeling.
If GIMP isn't missing any particular features you need, you may just want to steel yourself and get used to the new work flow. In any event, good luck! ๐