I remember a friend of mine signing a birthday card with a handwritten gnupgp signature ... thats geeky those fancy fanboy phones are not.

While I agree with you that the "default" FileField implementation is not very well suited for more advanced use cases, I have to strongly disagree that this is actually a problem. Beeing django and not rails you can very easily enhance or even replace every part of the framework without writing everything from scratch. This partly due to the nature of python and partly due to the design of the framework. And I really cannot see why the implementation of the FileField is in anyway newspaper related???