Part of the problem is the "I don't get something tangible for my money." Never mind you're receiving a lot of, you know, information or anything. People want something they can point to and be like "Yo, I bought that." That's hard to do with eBooks, so you have to consistently price them lower.
Also, marketing to programmers/the HN crowd is significantly harder than a mainstream crowd because you have to deal with the Nick Burns Effect: you are an idiot and I could totally do everything better than you in a weekend. Rails 3 Upgrade Handbook? Received hate mail for weeks about how I should have made it free, how I charge too much, how the book isn't available in HTML, how they could write the whole thing in a weekend using an automated script (seriously), etc. I still get the occasional e-mail about how "I'm probably going to write my own FREE AND OPEN SOURCE guide (which is MORALLY SUPERIOR TO YOURS), so you should just give me a free copy of yours to help you fix any errors." It's a culture issue that's difficult to work around.
Even worse, selling them on something that isn't essential to their job function is difficult (most people don't write eBooks for a living), and the problem with http://authoringebooks.com is compounded with the fact that I'm competing against people who are entrenched and SEO'd out the butt. I don't have time to sit around and tweak my SEO stuff all day, so my organic Google traffic is significantly lower than what it would be if I were more visible.
And also, the market for those who want to write a technical ebook may not be as big as I originally anticipated. :)
So, uh yeah, I agree. Pathological customer bad.
There exist programmers who happily pay $50+ for ebooks. Empirically, there are enough of them to support successful businesses.
P.S. See also consulting rates, writing OSS, etc. After somebody hits my patience for free support I just quote my daily rate at them. If they don't like it, well, enjoy the code.
People make a lot of money selling eBooks, including to programmers. (Indeed, the recent change in the market is that thanks to the Kindle you can actually do well selling books which don't cost ~$50 and/or fiction.) Ask Amy Hoy, who cowrote a fairly successful one with her husband about JS performance. Your problem is not your pricing. Your problem is that your marketing does not communicate value sufficient to justify a higher pricing.
If you hear someone on HN or demographically similar say "That's too much money!", file them away in the pathological customer bin.
Look at the difference between your site and these sites, then optimize accordingly:
http://javascriptrocks.com/performance/
http://www.startupbook.net/
http://peepcode.com/products/meet-rails-3-i <-- not an ebook, but similar