The problem is that you need jailbroken iphone, which wont be so easy for average joe. There wont be final resolution before Apple also learns that restricting so much is a bad decision.
Out of curiosity, have you even jailbroken an iPhone?
I'm going to say that for an average Joe, jailbreaking an iPhone is *not* a problem assuming said average Joe both knows how to read and owns a computer with internet access.
Maybe the "below-average" Joes who have an iPhone, but either do not know how to read or do not have a computer with internet access would have a problem figuring out how to jailbreak, but the truly average ones, they won't have any trouble at all.