Games eventually stop getting updates. They're proprietaty software so they're always in danger of becoming incompatible with newer systems. This is true even on Windows: older games regularly fail to work on Windows 10 in my experience and many didn't recover after hunting down the missing DirectX stuff. It's gonna be ironic if Wine becomes the best way to play these games one day.

In a way, this is the whole point of the emulation community. Proprietary software was developed for really old systems and they don't work on modern computers. The old systems had to be emulated as virtual machines on top of which the old software could run.