I'm of the opinion that, since Dunbar's number is a purely biological limitation, there's no reason to think that computer-assisted reputation can't scale to much larger groups of people. I think Cory Doctorow is right to be worried that an authoritarian government could use reputation as a tool of coercion (and this is why we should worry about things like government collection of phone metadata). However, I think it's also worth considering that reputation could be used as a tool by the people to obtain some accountability from the rich and powerful, and to help distinguish grass-roots support from astroturf. (I went so far as to create a site, http://polink.org, as a sort of collaborative graph database of how powerful people and organizations are connected to each other. It's one of those side projects I feel like I should get back to and work on one of these days.)
One of the reasons I think computer-assisted reputation hasn't taken off is that it's actually kind of hard to implement a good reputation engine, or even agree on what sort of properties a good reputation system ought to have. A lot of awful reputation systems have taught the technology industry to have very low expectations, which is a shame because I think they can be very powerful if implemented well and used correctly.