This is great.
While tech bloggers often complain that iOS is too basic or isn't changing fast enough, there's a considerable segment of consumers that remain intimidated by the iPhone (and smartphones in general). I'd love to see Apple making a more concerted effort to reach those users, not by airing ads showing off all the crazy, incredible things you can do with an iPhone, but by showing less tech-savvy users that an iPhone can just as well function as an easy-to-use dumbphone replacement. Not all dumbphone users are remaining with cheap phones because they don't have the money to upgrade. Many are of the attitude that the iPhone is too complex for their needs, and Apple could do well to counter that.
Of course, that push would have to be supported with a more polished version of iOS that doesn't confuse inexperienced users. Wiggle mode definitely needs to be off by default.
Neat. I always love reading these, and performing them informally with relatives of mine when I get the chance. I don't fully agree with all of your proposed solutions (e.g. I think the unintuitive nature of the tabs interface in Safari can be attacked at a more fundamental level, and demonstrated explicitly the first time, as opposed to a separate 'mode' that is really an interface band-aid), but enjoyed reading it quite a bit. The fact that several of the stock 'data app' icons (weather, stocks, clock), really do imply a live data display, when in fact the icons are static, had never occurred to me before.
Cool blog post! There are a few things I recognize, from when I had to help my grandfather with his iPhone.
I’m the OP and forgot to give credit to Garrett Murray for the discovery. He adds some interesting notes on his blog as well: http://log.maniacalrage.net/post/45711319181/rentzsch-my-mother-tries-an-iphone (sorry Garrett!)