Who knows. More frankly, who cares. You're asking a wide, and far too broad variety of questions.
"Will it work on this DOS based operating system that's old enough to be considered an antique vehicle in most federal areas?"
Probably not in most cases. Besides, why would you want to inflict that on yourself?
"Will it work on this NT based kernel that's old enough to be able to drink in the USA?"
Maybe, but don't expect any realistic support or miracles. Besides, Windows 2000 is better and cooler.
"Will it work on a current NT Kernel that hasn't really changed since Windows 7?"
Yeah, yeh it might. I would suggest
alternatives, though and leaving Microsoft behind.