Taking the last point first - the right certainly seems to have suceeded with a them vs. us viewpoint. In point of fact when there was an actual left movement (as opposed to individual leftists) I think it succeeded by portraying the owning class as useless parasites, and workers as the people who actually got things done. So I think the point here is that a us vs. them attitude might be successful - it is the "downtrodden" part that is the loser here. Just speculating, but so is your friend and so are you.
I will note that in the single payer movements I've been involved in,
it always seemed to me that exessive emphasis was place on the plight of the uninsured, and not enough on the fact that people with health insurance can't get care. I always thought that the way to win would have been to focus more on the fact most people have to reason to be certain they would get care if really sick - regardless of whether or not they are insured, that this is because of the insurance companies who essentially play the role of preventing people from getting health care. Demonize the insurance companies; them vs. us. useless parasites living at the expense of hard working ordinary folk. Would it have been any more successful than what was actually used? Who the hell the knows. But I think that should at least be considered before we start throwing "us vs. them" out of our tool box.
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