Part of it is finding a good drawing tablet and good software for it. A $40 wacom tablet and whats out there for free/cheap on OSX currently doesn't work -- it

Part of it is finding a good drawing tablet and good software for it. A $40 wacom tablet and whats out there for free/cheap on OSX currently doesn't work -- it takes too much frustration compared to compared to the intuitive interface of pen+paper. You'd need something with the intuitiveness of MS Paint, which is hard. MS Paint's intuitive program model is world class.