I have been saying that we need a “dosbox for the next generation”. Wine is great but due to Apple dropping 64 bit support it’s been decidedly less useful for me.
DosBox works well enough for most pre-Windows stuff, DosBox-X can handle the Windows 95 era well enough, but Windows 2000-Windows 7 stuff is actually kind of hard to get fully working on modern computers, and I feel emulation has not been able to keep up.
I wish a lot of success on this project. It would be great to get Jazz Jackrabbit 2 working on my Mac without mucking with VMWare.
Try `gcenx` distribution of wine with crossover patches (https://github.com/Gcenx/homebrew-wine).
Work fine on M1, enough to play Heroes of Might and Magic III with various mods. I haven't tried playing the Jazz2 though.