Maybe I misunderstand (though I also think I understand teh issues involved pretty well), or maybe one or the other or both of us are communicating poorly.
How would you distinguish a trusted, encrypted, and untrusted channels, say?
In the context of sharing public keys, I'd say you merely need authentication. Web of Trust being one possible mechanism. This isn't a particularly advanced topic.
Relevant to my original post, information about whether the connection should be encrypted also merely needs to be authenticated, not encrypted itself. Of course, the HSTS preloading site uses HTTPS (with encryption) because it's easy and why not.
