Installing 25 year old binaries on Linux is rather interesting - relevant for stuff like some of the old Loki ports. Problem is mostly that they've been written with kernel 2.2 in mind, which does have different behaviour for quite a few things - you generally can find old libc versions compatible with the binary, but those libc versions don't necessarily play nice with the kernel.
There are some compatibility flags which made things work last time I checked - but not sure if that's the case, and it definitely won't work forever, given that 32bit x86 support is likely to be dropped eventually.
I hired into a community college IT dept ~2000. Manager told me they were a Windows shop. Ha np. I proceeded to replace 3/4 of their server room with Linux. email, cd servers, file servers, web servers, db2, PeopleSoft(gack!). I was working on a cs degree which they paid for about half
Windows can't even install its own old products! I remember back when I had to upgrade systems from XP to 7 and the users needed IE8 in able to use some internal websites. Microsoft was like "Fuck you, you can only use IE9 or above" there was literally no way to download IE8.
I also hate it when they only make shit available through the Windows Store or another convoluted process. No more downloading a simple EXE or MSI and double clicking it!
Windows: nope, too old. Find a version that's compatible with your current installation.
Trust me, I tried playing some old CD games from my dad's shed on Windows 10 for such a long time, it wouldn't even let me do that without having to rely on a virtual machine. Most of those games were in French and German, btw.