Yup. The right thing for him to do would be to write a technical book and sell it. He has his emacs tutorial, but his website already has a bunch of poorly placed ad units on it.
He's literally competing with his own tutorial by selling other sections of his webpage at probably less than $2 cpm. If he optimized his page to sell the tutorial he would earn more than $2 cpm per unit on that. The 'around the web' units are probably not even being managed because it looks like they are set to the defaults for general audiences, which is inappropriate.
What I would do:
1. Redesign page
2. Kill ads
3. Raise price to $30 or more
4. Aim for 2% conversion (no clue how many of those numbers are unique sessions)
5. 2% x 240,000 = 4800 sales -- 4800 * $30 = $144k before fees and taxes
That's wildly optimistic given that a lot would have to be done to the site and that the people looking for free emacs tutorials may not line up perfectly with those willing to pay for it, but if it's legitimately a good tutorial there's an opportunity there. Even a more realistic .2% conversion would still be an OK living for the guy.
He could even get started by quoting one of the other dudes in this thread who said that it was good.
The ads that he has on the page are pennies and it's hard to actually find the tutorial that he charges for. That he might be a jerk is actually totally fine. You would just have to work it into the copy as him having a maverick attitude and being a no-nonsense technical guy, which works well for selling to people who are technical.
