The answer to this specific Meta question is, generally, going to be "No."
But that is not what is really being discussed here, at least from my point of view.
The QA that spawned this meta discussion so late in the day was prompted by a real-world sub question in an existing Retro discussion. People are going to come to Retro with questions and confusion about the general notion of downloading images for personal retro-computing reasons.
In general, these people do not need a lawyer's answer for the question at hand. Just like over on Photography SE, you don't need to be a lawyer to answer "do my photos belong to me" or "should I get a release form signed" (both typical and well-answered questions over there). Yes, we should defer to a legal expert when discussing specifics, and such answers are encouraged to say this. But many of those questions related to copyright can be answered well enough for the answers to have utility for the audience, now and into the future. Again, this is true for Retro as it is for Photography and other SE sites.
The purpose of guidelines is not to collect a bunch of criteria with which to beat people with. The purpose of guidelines is to support the notion of useful questions and answers that are relevant to our interests.
We should be promoting useful QA that serves the needs of the community, not getting tied up in knots over categorizations. At the heart of this discussion is the question "is this QA good for the community, and does it serve the community?" Does it address a specific concern, and can it be addressed in a sufficiently specific manner?
That is, while in general legal questions (especially those that have a strong regional component) are probably not on-topic for Retro, a general question about how the Retro community might gain access to copyrighted material is on topic. Even if it is a special case, we should always be wary of categorization scope creep.
In conclusion:
- Generally speaking, most questions that hinge on the legalities of the hobby are going to be off-topic.
- That being said, the great majority of such questions are going to be variations on a theme.
- The theme is going to be variations on "Is it generally legal to download and possess commercial software that appears to abandoned?"
- These questions are going to be common. They are also very straightforward to answer because of the nature of the international law at play.
- Because of how a huge majority of countries have signed onto the law, it is pretty easy to provide a general, global answer: "Generally, no."
- Almost every SE site where the interest intersects with copyright have similar questions with similar answers.