You can’t run a 30 year old driver in Windows, nor a 10 year old in all likelihood.

Microsoft prioritizes userspace compatibility, but their driver models have changed (relatively) frequently.

If you are a Crowdstrike customer you can’t run anything today.

For apple you just need to be an apple customer, they do a good job on crashing computers with their OSX updates like Sonoma. I remember my first macbook pro retina couldn’t go to sleep because it wouldn’t wake up till apple decided to release a fix for it. Good thing they don’t make server OSes.

I remember fearing every OSX update because until they switched to just shipping read-only partition images you had considerable chance of hitting a bug in Installer.app that resulted in infinite loop... (the bug existed since ~10.6 until they switched to image-based updates...)

30 years ago would be 1994. Were there any 32-bit Windows games in 1994 other than the version of FreeCell included with Win32s?

16-bit games (for DOS or Windows) won't run natively under Windows 11 because there's no 32-bit version of Windows 11 and switching a 64-bit CPU back to legacy mode to get access to the 16-bit execution modes is painful.

Maybe. Have you tried? 30 year old games often did not implement delta timing, so they advance ridiculously fast on modern processors. Or the games required a memory mode not supported by modern Windows (see real mode, expanded memory, protected mode), requiring DOSBox or other emulator to run today.

DOSBox runs on Mac too, incidentally.

A 10 year old driver would crash your system, and you can't install some VM like you can with some game. Not that great prioritization