The big reason why I think he's wrong is that I think the default behavior is correct: the vast majority of people don't understand the complexities of a Man-In-The-Middle attack and how that can affect any self-signed certificate. However, I totally understand his desire for more encryption.
I'm pretty annoyed at the fact that at the moment, I'm pretty sure that all non-encrypted traffic on the internet is being logged and scanned at some level by multiple governments. I don't like that at all. Encryption is the only way around it.
But we've had technologies for implementing encryption on-the-fly where we don't care about the possibility of an MITM attack for yonks. Just use DH key exchange as a handshake and then use that as the key for a stream cipher. No need for certificates at all. You get strong encryption between endpoints, and acknowledge that you're potentially subject to a MITM attack. You can even combine it with some advanced DNS checking to minimize the chance that your company/government's proxy is MITM-inspecting every connection. The only problem here is that there isn't a clean URL handler supported by RFCs that is available that I know of.
Why not just start one?
httpe(HTTP Encoded, but not Secure)?