I am obviously dismissive of Raymond. I think Raymond has been a terrible figurehead for open source. Due to my bias, my reading of "Cathedral" is that Raymond saw Linux getting a huge amount of attention and wrote an essay that is essentially "Me too, I wrote fetchmail".
I agree with that, but still think CATB was a pretty good paper: I don't think they're two completely exclusive concepts. Along the same lines, I respect some things about RMS and what he's done, and disagree strongly with others. He is also not a very good advocate for open source (err.. free software): perhaps that's why ESR got some traction - he was not great, but better than the others. At least he wasn't opposed to people making money to the point of personally offending them.
I think that's a bit too dismissive: he wrote effectively (as you say) and convincingly about free software in a way that no one else was doing at the time, and for an audience that was not just other hackers. That's pretty good in and of itself, even if he didn't have any brilliant insights.