So far, "freedom of App Store speech" and money don't seem to be correlated at all. (Or all the millionaires on OpenMoko and Cydia are being quiet to prevent a gold rush on their turf.)
I think the only instance where Apple's guidelines are prohibitive to making a living is porn. I for one would be a thousand times more likely to pay for porn on the trusted platform that is Apple, rather than on some dubious website.
Is it possible to use this as an advantage against established app stores? Or is Google already established as the platform to be on for mobile porn? (I can't check first hand, thanks to Google's GeoIP madness.)