If it makes you feel any better, there are approximately 5000 404s in links "in the wild" (according to google crawl error stats) that I have the capability of improving the quality of the redirect for. I may not be able to get 100% accuracy on the redirect, but I can get the user to an issue page of the archive where they can click the story they intended to see. The problem is that there is no metadata associated with those links to get a better idea of what story it was. news1.html isn't terribly descriptive.
To put this in perspective, I get approximately 40000 unique 404s from spiders every day for things that simply don't exist and never did.