What exactly prevents someone from installing an old version of Windows and then the necessary legacy drivers, taking those same precautions?
Nothing. Nothing does.
Nothing. Nothing does.
If you still have the drivers handy - sure. I personally would trust older versions of Linux more than older versions of Windows though. And I say that as someone that is also typing this comment from a Windows desktop.
Newer old versions rely on Microsoft to activate them. Given the trajectory the indistry is moving toward, I don't have a lot of confidence that will last indefinitely.
More and more features these days are getting inextricably tied to the cloud, and it's becoming trickier to create offline installation media even for the ones that aren't.