Comment by amalcon

I actually have already done this -- or, rather, helped someone else to do this. The individual in question was an academic with a license for a rather old version of a particular piece of domain-specific software, which would only run on Windows 95/98/ME. As he taught at a small school, his budget wasn't exactly infinite, so he kept an old Windows 98 machine around to run that software.

Turned out, it ran great on Wine. Actually, the performance even improved because the hardware was so much newer.