"Pretty well" is doing a lot of work. I have no horse in the race. I just run native on MacOS or Linux. Haven't run any Windows in a number of years. (I don't really game much and would just use my Xbox if I really wanted to--though that mostly functions as a DVD player these days.)
But if "pretty well" causes the random administrative person to have issues with doing their job or increases IT support costs, it will be off the menu pretty quickly. We'll see. A lot of things are different from the last round of we're going to Linux in Europe.
We've come a long way in the last 2 years. We're at a point where MOST Windows software works flawlessly. I said "pretty well" as theres no doubt a few that don't and it'd be a bit disingenuous for me to suggest otherwise.
I certainly wouldn't come into this with knowledge on wine older than 2 years and make a snap decision though as its a totally different landscape - no weird quirkiness and tweaking needed for the vast majority of applications anymore.
Nowadays, pretty well a lot of times means really well, maybe even better than on Windows. See Windows games running faster on Linux through Wine.