There is the joke that even a broken watch is correct twice a day. I do think his communication style, his use of hyperbole, and his unwillingness to bring the listener 'along' work against him in most situations. However, he does have a self consistent line of reasoning as far as I've been able to discern for all of his positions.

But lets step back from the messenger for a moment and look at the message. Richard's rant on cellphones is predicated, in part, that they can be used as surveillance devices. The engineering of a cell phone network is such that it presents, perhaps as an 'attractive nuisance'[1], the ability to extract surveillance data. This has nothing to do with whether or not the software in the phone is "free", rather it has everything to do with how that software is used.

So a question that does not come up often, and I have yet to see in print, is this, "If all software was 'free' and 'open' how would that change anything?" So if the source code to the handsets is "free" and the source code to the base stations is "free" and the PSTN software is "free", what changes? SIP based phones have the same surveillance capabilities as GSM phones and one can put together a nominally 'free' stack for such a phone network. I'm afraid I don't have any good answers here.

[1] http://definitions.uslegal.com/a/attractive-nuisance/ although in our case the 'children' here are Law Enforcement Officers (LEOs) who don't have the resources to send someone out to follow you around.