It depends on which 20 years you’re talking about. Some of us here have been using Linux long enough to remember the change in the late 90s to use elf format. I don’t think a Linux from after the change can run anything from before.
We're not talking about drivers, we're talking about applications. You can take an application compiled back in 2005 and run it on a modern Linux machine, as long as the machine architecture is the same.
I assumed the machine would require a custom driver. Else it's extremely unlikely the app was broken as early as 2006 (so on Windows Vista) without their research group having some sort of support contract. Software would have been barely 4 years old at that point.
Yes. As long as it includes all its dependencies, it should work because the kernel never deprecates system calls.