I think there's more to it than bringing skills (hardware, python) to people. Modern hardware isn't made to be hacked, and I'd wager that almost no amount of Python education will help you learn to use your iPhone more effectively. Most modern closed-source software is pretty user-hostile if you want to do anything more than exactly what the authors intended.
For examples of hardware that's made with modification in mind, see the Chumby or the Novena or the Chip. For software...that was kind of the selling point of Smalltalk, I think? Also Lisp machines--basically, an environment that doesn't really draw a distinction between "programming" and "using".