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
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.
I could imagine the process being relatively easy if you have a pre-existing relationship with a publisher like O'Reilly: send me the contract, here are the essay URLs (which have already been proofread), do the typesetting, and send the book out into the world.
In actuality I suppose it's not that simple.