This seems to me to be an edge case. We definitely don't want you asking how to play a video game, or how to win one, or the place will wind up looking like Gamefaqs, with game spoilers crowding anything else out. On the other hand, asking how to run an older program on a newer OS should be SU material. I think you've got a legitimate question on a sensitive topic.
I'd suggest looking at the documentation to see what it originally ran on, and if possible trying to run it in some sort of compatibility mode. When you've done that, repost the question without mentioning the program by name, asking for suggestions and assistance.
I don't consider this an end run around the rules, but a way of asking a legitimate question by removing the illegitimate elements.