Some of those essays are good enough that they're worth resubmitting every year or so, both for people who haven't read them yet, and to see what new points come out in the discussion.
I would agree. I've been a lurker on HN for a couple years and the recent PG post about creating wealth was new to me. It was a wonderful post, old as it may be, and much more useful to me (a developer) than multiple posts about another acquisition.
Can old links be re-posted after a certain period of time passes?
If so, maybe auto-add a prefix, "REPOST: Article Title", for any link that's re-submitted. That way people who've seen it before can ignore clicking on it, while those who haven't seen it will now have the opportunity to read it.
EDIT: BvS already posted a link to a Reddit post with the same idea.
I agree with your points. The only thing that I would ask for is to date new submissions of old posts with a label such as [2004] so that readers can immediately grasp whether it is a new essay or an old one.
Essays, like good literature, become more relevant and certain times. A major event could happen (Groupon turning down Google) and a PG essay could shed some light on the situation, even if it was written years ago.
Likewise, new situations can cast a different light on what was once written. HNers posting relevant and timely links to old essays is a good thing.
I agree that the discussion, especially the questioning and answering (but not so much the posturing) is especially good.
But can we limit it to one resubmit per year? After a couple times in the same year, my patience grows thin. After all, HN has a lot of really good essayists out there, folks who can be just as helpful. As nice as PG is, we don't want to give him too much exposure. After a while anybody can start to sound repetitious, like when they go on and on about something. Sort of like repeating themselves. Over and over again. The same thing.