They want shinies, they want fast transfers, they might won over by ideology, but probably not the ideology of libertarianism. They want to use the system that their favorite site uses, and they want to use the system their friends use. This by the way probably describes how mainstream males think too.
Shinies:
Lets face it. Bitcoin, in its current state, is not shiny. To make a metaphor, it looks like a very advanced piece of technology with wires going everywhere. Contrast this with the "Apple look".
100 private keys is probably NOT the way to go. It is complicated, and ugly (it could be an option but not standard(
Proposal: One private key should be standard. It should not be in hex, bas64, or anything else ugly. One thing that could work would be a sort of dictionary encoding, where every 20 bits or whatever is mapped to a word. The word in the dictionary would have to be carefully selected to be positive, or at least neutral. If this is chosen, there should be a "generate new address", so that people could click until they found one they were satisfied with.