1. I don't think Pournelle is against ebooks or giving away ebooks as a principle - he is after all a technologist at heart. Readers may know him from his sf novels, but in IT he is mostly known for his Chaos Manor columns (which he apparently still writes) that used to appear in the classic IT mag Byte, and they are still held up as a standard for hands-on tech reporting. He's an iPad aficionado, and I think he knows where the future lies in terms of where we'll go with our reading.
When I read Pournelle's opinion, his beef isn't giving away books for free, but how Doctorow's position on setting his works free *affected* other authors who, because they don't have the type of exposure Doctorow has, will not benefit from having their works put out there.
Here is Pournelle's take on the Scribd case:
Chaos Manor Reviews Column 326, Part 1, September 4, 2007. Although the main premise was that of privacy, and I realize we're not talking about privacy here, but it does highlight the thinking behind why there are people who cannot and will not subscribe entirely to the notion that giving away books for free will definitely generate revenue for the authors.
I've spoken to authors who are genuinely nervous about having their works put out there, even for a limited time. Each person who've read it for free is a lost sale. They don't have the clout that Doctorow has (although to be fair, he has had a head start, and he's tech savvy). There are authors who don't do anything but write, and leave everything else to their agents. How are they going to go social media to promote their work?
Having said that, I still think that's the way to go in the future. I believe in an open internet market, the good stuff will float to the top, while remaining viable for niche authors to find their audiences.
2. Pricing: The problem is to have a model where the authors get their due. While it can get pretty lazy to equate the similarities between this fight and the one that digital music had some time back (they are not completely analogous), but one thing that we can learn from music is when a proper mechanism for fair reward is set up, nobody will complain (too much). There is no such structure in place because there isn't a viable centralized service role for ebooks such as the role that iTunes is playing for the music industry. Amazon is nowhere near the dominant position in the market that iTunes is.