If you had to open an app on your phone at each login you'd get crazy real fast :)
I do like your analogy tho. Digital music is a breeze to buy nowadays. Moxie seems to appear as covertly saying its misguided to donate money to GnuPG so that it finally gets good, because, you know, not-moxie-made.
The.. what was it called? Redphone? Whisper? and various other projects - while very cool - didnt achieve even as much popularity as GnuPG (which in itself is far from greatly useable).
I know of one tech that has a chance right now and thats U2F/Fido. It allows for building a framework (being GnuPG or otherwise) around it that's both secure and works for everyone. Why? Because fucking gmail supports it that why. It has nothing to do with the actual tech. It has to do with support. It has to do with my iphone, android, whatever, working with it seamlessly. It a lot to do with "slapping a GUI" at the right places.