Has it come on leaps and bounds since then?
The difference between the past and now is that it lets you use your current native steam client and still run games through wine, in the past you had to run a separate steam client in each wineprefix and you'd end up with steam installed for each game.
The addition of DXVK makes directx10/11 games really speedy, runs great! World of Warcraft runs better in DXVK in its dx11 mode than what it did with OpenGL when they still offered that.
The "game-breaking" thing is usually DRM like denuvo though.
Games run smoothly, no frame rate issues, no Wine to setup manually, no Wine configuration files to play with. It just works.
Then I tried this one more time the summer I started college (3 years ago?) It was working but lagging, and sound wasn't working, and some controls weren't working and it was randomly crashing. But it was still playable.
Then I tried it one more time this summer when I graduated from college. I spent an entire week and couldn't get it done. At some point I was applying patches in C and recompiling Wine which apparently fixed something? I also spent a lot of time trying to find the Wine version and Skyrin executable I used 7 years ago. For the love of God I, a CS graduate, couldn't get something my high school self done.
If you find something working in Wine, save the executable and Wine version. There is no guarantee any other combination will work. But I swear to god, 7 years ago whatever Wine+Skyrim combo I used was working flawlessly, I can't imagine it working any better in Windows back then.