It seems like you guys tl;dr'ed this one a bit. Here's the relevant part:
The point of the advert is to pre-emptively debunk gross misconceptions about Bitcoin.
The point isn't to get more users or inflate the price of BTC or what have you. The point is to counter the coming tide of "bitcoin is for criminals" propaganda.
Whether this idea will be effective in terms of bang per buck (or rather, per BTC), I'm not sure, but the current user-friendliness of the client and other bitcoin-related tools is irrelevant here.