Here's a request that's unlikely to be fulfilled but one I'll make anyway: assemble an essay collection aimed at high school / college students. In my ideal world, it would contain in about this order:

1) What You'll Wish You'd Known

2) What You Can't Say

3) Disconnecting Distraction

4) The Age of the Essay

5) Why Nerds are Unpopular

6) Writing, Briefly

7) Why Smart People Have Bad Ideas

8) Good and Bad Procrastination

9) How to Do What You Love

10) See Randomness

11) The Power of the Marginal

12) How Art Can Be Good

13) Taste for Makers

14) Two Kinds of Judgement

15) Stuff

There's obviously some overlap with this list and Hackers & Painters. But I think this grouping would be much more useful for the general population; most freshmen aren't as keen on programming language discussions.

I often use the first three essays listed above in the freshman comp classes I teach, and they often yield interesting reactions from students. Sometimes we venture into "The Age of the Essay" and "Stuff." Students who are especially interested in why high school is structured the way it is often get pointers to "Why Nerds Are Unpopular."

If you know anyone at O'Reilly, you can tell them they'd get about 50 copies a semester ordered. That's probably pretty small time, but I suppose something is better than nothing.