Speaking as a full-time Linux users since 2016: I found that getting old (i.e. unmaintained) native Linux games to work again is MUCH harder than running their Windows version. E.g., I spent hours trying to get the Linux port of Unreal Gold to work with no luck, and in the end had to give up and run the Windows version under Wine. There is just so much change on the Linux desktop that old software is just not going to behave well. Not only do you usually need to reproduce the entire userspace from the time the game is released (and of the distro that it was built against), but changes in display APIs (Xinerama, XRandR, SDL versions...) often result in full-screen or resolution problems.

This is a project I wrote to work around exactly issues like this: https://github.com/CyberShadow/hax11