1. You probably don't need it. I don't know about the legalities involved here or what the specific license is, but there's probably a trivial way to circumvent the hardware requirement, especially with a VM. Back when Windows 2000 was a thing, people were still using MD5, and nobody was using secure elements. Worst case scenario, they've got some of the actual program logic on there, and you'll have to either reverse it or replace it. Again, not commenting on the legalities here, but seeing how the software was (presumably) legally licensed and the company is long gone, it couldn't hurt to ask the lawyers whether they think it's safe.

2. You can pass a parallel port through to a VM if you really must.