Can't say that Windows 11 compatibility on this regard is any way better. Anything pre Dx-9 is somewhat broken one way or another.
I've recently found about Dreamm[1] by AAron Giles (a well known emulator developer) which is basically a very lightweight os-indipendent reimplementation of some windows and directx calls specifically for some Lucasarts games written during that time period, It would be nice to see a similar project expanding in such direction without having to reinvent Wine and/or Proton.
It's definitely game-dependent. In a few cases I've found it was easier to rebuy a game on GOG, like Dino Crisis or '98 Resident Evil 2 (whose re-releases indeed run on win11 flawlessly while they're quite problematic on Proton) rather than messing with their original cd/dvds.
On the other hand the Sega arcade ports from the same time period (Sega Rally 1&2, Daytona USA Deluxe, Manx TT Superbike Virtua Striker, etc.) are definitely less problematic on Wine/Proton rather than Win11.
I've recently found about Dreamm[1] by AAron Giles (a well known emulator developer) which is basically a very lightweight os-indipendent reimplementation of some windows and directx calls specifically for some Lucasarts games written during that time period, It would be nice to see a similar project expanding in such direction without having to reinvent Wine and/or Proton.
https://dreamm.aarongiles.com