You've got Black and White working? I've smashed my head against that one before but never got it going.
The issue is that the copy protections check for a physical disk (with various methods) sometimes "Windows" ISO tools work better (CDEmu CloneDrive...) you would need to run them in the same wine prefix. But the easier way might be to find a nocd "patch" for your application ;)
CD Copy Protection & WINE ( kbin.run )
Recently I have been trying to play my old games (Worms, Sims, Black & White, etc..) on my Steam Deck....
If you are looking for a new obsession ( youtu.be )
This video is a deep dive into HVAC systems, but each of his videos are pretty interesting and about different topics.