But it also serves to legitimize the protestors' viewpoints.

This only works if you optimize for positive attention in media and academia. While I can see getting positive or very positive coverage from both, let me ask you, do you think the Ivy League professor or the media mogul, regardless of what noises they are making, really have it in their best interest something that corresponds to an idealised, rationally cleaned up version, of what OWSers really want? Even if the believe themselves to be pursuing something, what has LW taught us of self-deception and selection effects?

Once you have serious discussion, you can start assembling voting blocs and existing candidates who do support your views (the progressive party seems a likely ally.) As the discussion grows more legitimate, and the voters grow more confident, your political allies gain more power. And they in turn can use that power to further spread the discussion.

This is essentially part of the theory behind why a democratic process, or at least modern parliamentary democracy, should work. It is here that I also think the failure point is. I think there are systemic issues with which opinions and programs can and which can not cascade in this fashion.