I think this is probably the key contentious issue for this forum to focus on. His general argument makes sense: autonomy is a basic human psychological need, technology necessitates a strongly linked society which denies autonomy therefore technology is bad (to compress 232 paragraphs down to a single sentence). Some questions to think about:
1. What is regulation? We tend to think of it as government regulation, and when advocating government-free societies fall back on some sort of boycotts or community action as an alternative. While such alternative regulation has advantages in that, if practical, it is far more agile and incorruptible, is it really any better in terms of not denying autonomy? Social coercion controls us in many ways, from what clothes we wear and how our homes are constructed (even beyond the rules imposed by restrictive building codes) to how we speak and even think, but does the fact that submitting to social coercion is philosophically voluntary mean anything from a psychological point of view?
2. Is it possible to create a social system where rules of any sort beyond private property-style restrictions are largely unnecessary? It can be seen that as society becomes more and more complex our actions affect more and more people - for example, due to the urban density issue what we do affects more and more of our neighbors, due to technology we have less and less privacy in our personal lives, the industrial pollution that is a necessary consequence of much of modern society arguably affects the whole world, etc. But is there some way to make the situation less restrictive? If, for example, jobs were mostly online it could make people much more physically mobile and able to live beside only like-minded people. Putting more social activity on the internet also helps. In the most extreme case, furthering space exploration can separate people into cultural communities completely (cf. ethnic streaming in Peter F. Hamilton's Night's Dawn Trilogy, if anyone's read that). What can we practically do to maintain the sphere of impregnable autonomy within our lives that we seem to need?
3. (focusing on another argument in the manifesto) Internet communities based on common interests could potentially replace the small tribal groups that we would see in paleolithic society. But for that to happen it would be necessary for such communities to be reasonably small - less than Dunbar's number (http://en.wikipedia.org/wiki/Dunbar's_number) of 150 - so everyone can have an identity. Is that practical? Right now the minimum size for an internet community seems to be in the low thousands since people only spend a few minutes of their time a day in one, but can that change? MMO guilds with <200 members seem to be holding their own just fine, since they are based in a setting that people tend to spend >1h a day of their lives in, so is that the direction we'll be going in the future?