Uhh WINE so unreliable. The summer when I started high school (like 7 years ago or something like that?) I played Skyrim in WINE in my shitty ass laptop. No kidding, it was an extremely good experience. My laptop was ~$800 and wasn't a gaming PC. I was running archlinux with some unknown version of WINE. The setup was super easy, I don't remember spending time on instaling Skyrim. The game was 100% working.

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.