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Excellent post -- this sort of context is a great addition to the debate.
Speaking for myself, as both a you- and self-labeled optimist, I'd like to make two observations.
First, you ascribe to the pessimists the view that the internet is "... forcing individuals and industries to completely reconsider the way they live their lives or organize their business affairs." You say that like it's a bad thing.
This sort of re-consideration in light of new capabilities, as wrenching as such a thing can be, has nevertheless historically led to general social improvement (cf. the printing press or steam power). If the generation being disrupted were allowed veto power over novelty, nothing would ever undergo radical change. The fact that there is such a re-consideration, and that it is both widespread and mandatory, is the engine of the positive change that many of the optimists, including me, believe internet adoption will produce.
Second, you are right in noting the obsession with Wikipedia amongst the pessimists. I have a theory as to why that is.
In the 1980s and 1990s, evidence for the viability of open collaboration was mainly confined to free software (later labeled open source.) The main argument against free/open source software was "that can't work", but that argument began to fail with the success of Apache and Linux, and IBM's adoption of same.
At that point (ca. 1998) another excuse was needed, and it was: "Software is special." This argument had several facets: Code is uniquely suited to distributed collaboration, programmers are native to the internet, learning to code creates special social norms, and so on.
This excuse held until about 2004, and the growing general awareness of Wikipedia.
This is why Wikipedia is the object of such fascination and horror -- none of the excuses for ignoring open source software as a special case apply. If Wikipedia works -- which is to say if there is a general-purpose tool that can be used to create a public good of enormous, worldwide value, created by unpaid contributors *who judge their contributions and the results to be worthwhile* (Carr's concern, in particular) -- then nothing is going to hold back the general population from embracing those tools.
And if society tries using these tools, then each pessimist gets treated to their own special vision of the coming horror. Society will engage in exactly the re-consideration you've identified, no matter which experts lose their jobs (Keen), no matter how much it configures the existing social landscape (Siegel, in a reading that waves away the self-absorbtion), and that operates via economics of voluntary association rather than surplus labor value (Carr.)
Mass collaboration versus Individual Effort- There is no doubt that the internet has fostered mass collaboration efforts such as Wikipedia. But it has also fostered the grow of many individual economic efforts. Everyone can now have an internet store front that is accessible to the entire world. Ebay is an example of how individuals can sell products world wide. Currently, I am attempting to get replacement parts for a kayak. Without the internet the company offering the replacement parts would be very hard to find. With the internet they are accessible worldwide. The internet from the optimistic viewpoint is not simply about mass collaboration but the ability to reach anyone in the world. And that includes individual efforts to sell products and services.
Gift economy versus property rights- I am not sure of the origin of this one, but it appears to be a follow-up to "Mass collaboration versus Individual Effort". One can assume that with mass collaboration that this can be viewed as a gift economy since those participating in the mass collaboration effort are donating their time/money/labor.
From the optimistic/pessimistic viewpoint, I think this category misses the dynamics of what is happening. From the optimistic viewpoint, The Gift Economy column should be labeled "Adaptive Technology". The Adaptive Technology viewpoint (of which Mike Masnick at TechDirt is a major proponent) holds that if a new technology threatens your income stream, you need to adapt and change your business model. The pessimistic side currently labeled "property rights" should be labeled "Old School". The Old School model holds; if there is a technological threat to your business model, the solution is to change the law to frustrate the implementation of any technology that threatens your income stream. The obvious example of this trend was the passage of the Digital Millennium Copyright Act (DMCA).
If one upholds the concept of the free market, the optimists recognize that those selling products and services must adapt to the internet as a new technological opportunity. The pessimists on the other hand don't want real competition, instead they seek to frustrate the introduction of new technologies through the passage of self-serving laws to protect their interests, Additionally these laws are also used to create "toll booths" to exact unearned revenue. (corporate welfare).
I would definitely add John Robb's book or someone who is thinking about how the internet and open source production is re-shaping War, as well as someone like Bill Mitchell or Paul Virilio who would give some perspective as to how the internet is transforming Architecture and Urbanism.
I think you've made two interesting informational exclusions by not discussing:
1. those like Zittrain, who although more an optimist, sees both pluses and minuses. How about a category for balanced/realist?
2. Other disciplines like Architecture, Art, or War, which are all being transformed also.
As for Infotopia, though, I'm not sure if I'd place that in the optimist camp; Sunstein is much more nuanced and aware of the limitations of the net (as his position as a pessimist w/ Republic.com shows).
Also, consider adding David Weinberger's Everything is Miscellaneous and JZ's Future of the Internet (though I'm not sure FotI fits neatly into the dichotomy.)
http://techliberation.com/2008/03/23/review-of-...
http://techliberation.com/2008/03/30/apple-open...
http://techliberation.com/2008/04/12/another-pr...
Regarding Sunstein's latest book, Infotopia, I think it's interesting that Cass has begun pushing back against his own position as outlined in Republic.com. He's certainly still in the pessimist camp on some things, but he seems to have abandoned some of the gloom-and-doomism of Republic.com. My old 2001 review of that book can be found here:
http://www.cato.org/pubs/regulation/regv24n3/in...
Incidentally, one nice thing about Disqus is that you can edit your comments.
As a Sydney-based journalist and author of the recently released book, The Blogging Revolution (http://www.bloggingrevolution.com/), about the web in repressive regimes such as Cuba, Egypt, Iran, Syria, Saudi Arabia and China, the benefits of the net are unquestionable (something I explain more here: http://www.theaustralian.news.com.au/story/0,25...).
Shouldn't we be trying to better understand the web from a global perspective, rather than just focusing on the Western world?
I appreciate your comments and would be happy to "catch up" with whatever other books you care to suggest right after I get through the stack of 20 sitting on my desk right now. Yes, most of them are written by American authors, but that's been more than enough to keep me busy lately. But, again, I am happy to try to work others into the mix when I expand this essay into a magazine article as I am currently attempting to do.
That being said, I think many of the themes and perspectives found in these books are universally applicable. The intellectual struggle we see going on in these books is hardly unique to the U.S. Second, to the extent there are differences, I am always careful about commenting on foreign debates and policy issues precisely because the situation on the ground in some countries and continents IS different in that there might be nuanced cultural or economic considerations that I am unaware of. Stated differently, I don't want to look like the proverbial "arrogant American" who is telling the rest of the planet what he thinks of their policies or debates. At least not without doing my homework first !
Again, I appreciate your input and call for the inclusion of foreign perspectives, and I am eager to see your recommended reading lists.
[Note: I originally had "The Rise of the Network Society" by Manuel Castells (a Spanish writer) on the list but took it off because I had not read it since 2000. I might include it in the next edition of this essay after I have had a chance to go back through it again).
There is a lot of good books there to. Reading outside internet is possible!