Copyright infringement is only an issue when someone cares.

God, I wish more people understood this. Why on Earth would AOL care if someone distributed their 20 year old software enough to sue over it?

Until the TPP takes effect around 2019.

That's the Archive's business to deal with. They probably have exemptions (like they are allowed to host all those games legally).

This guy has gotten cease and desist letters from catheter companies as well as been sued for two billion dollars. Watch his talk on the matter, it is really great - https://www.youtube.com/watch?v=KSWqx8goqSY

AOL gave these things away in droves. They'd lose in court even if they tried.

I don't think that is as certain as you present it. Giving something away does not relinquish copyright, it merely passes one physical copy to someone else.

If what you state would be true then the GPL wouldn't have a leg to stand on, physical copies are rarely if ever used!

Giving an authorized copy to a third party doesn't involve any copying itself, and so copyright isn't really implicated here.

He does specifically state he'll accept ISO images as well as original disks.

The image would be a copy.

Otherwise, correct.