Re: Privacy
At the time he wrote that, the Internet was very much smaller & most people on it were geeks of one sort or another. So it was not exactly a dumb statement then. However AOL was connected about that time & the 'net started a long descent to what we see today, though there have been compensations along the way (Altavista & descendants, http, etc). PGP has always required some intelligent deployment. Enigmail might be just a plug-in but the real work is setting up & managing the public key infrastructure required to use it effectively as a day-to-day tool. Amongst a small circle of friends, acquaintances & colleagues that is manageable, but otherwise, forget it. And although there is now a halfway decent CA infrastructure for website certificates, that's still too hard to deploy universally for personal e-mail signing & encryption.
So non-TLS encryption is going to stick out like a sore thumb for a long long time, even TLS used in unusual contexts (not web, not IMAP etc).
Biting the hand that feeds IT
