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I feel like there is a logical connection between you getting sick and working on an OpenPGP implementation, but I cannot for the life of me figure out what that connection is.

Take a look at https://cryptup.org (disclaimer - my project). Encryption can be made easy.

RFC4880 may be ugly. Yet great design can still turn it into a good user experience.

I don't think anyone considers TCP/IP pretty. Who cares? When I open my browser, I see none of it.

Well, given that Google is giant, unbelievably powerful, and have a very significant share of email market - they could've pulled just about anything. If OpenPGP isn't good (and it's true that it has issues), they could've implemented and proposed a whole new standard that addresses existing shortcomings, evangelize/market it - and it's very likely others would've followed.