Random old stuff is available via Windows update. You’d be hard pressed to not have it just pop up and work.
Maybe for some old serial/parallel stuff you would have issues, but for anything USB? It’s gonna be on Windows update. The days of searching the internet for random drivers mostly died with Windows XP and pretty much completely died with Windows 7.
And back at that time if you installed any flavor of Linux you were lucky if the OS install didn’t fuck itself over, also God help you find drivers, assuming that they even existed. At least xp would function.
As of windows 10, windows will always function on pretty much any hardware out of the box. Some obscure Chinese WiFi dongles might have some issues, but main board drivers are always right there.
Linux users have this weird echo chamber where they seem to think that Linux just works. It can but it’s a 50/50 chance that it won’t and you’ll spend hours troubleshooting. Also os updates on Linux have a high probability of borking the entire os.
Windows, for all of it’s many many faults, generally does “just work”. It might not be perfect, but it will function.
And that’s the rub. You have to very specifically choose your hardware for Linux. Or at least you had to back then. It’s not quite so bad now, but back then it was a real showstopper. Especially broadcom. That caused me no end of issues back in the day.