This is my first diary here, and it's an expansion of some points I first made in comments. Bear with me!
I'm one of those people who isn't just interested in talking healthcare policy with people who already agree with me. So I frequently post various places (under a variety of pseudonyms) and argue healthcare issues with people like Libertarians and Republicans. I've collected some points from my experience that are obstacles in making headway on this issue. I'm sure most of us have had the frustrating experience of trying to convince a conservative family member about the need for reform.
1. The massive amount of false information that the Republicans and their sponsors have carefully planted in people's heads over the last few decades.
Whenever I argue this with people who aren't that informed, I always run into the complete BS about Canada, "rationing", how much "more" single-payer would supposedly cost, etc. When we present our arguments for a more socialized healthcare policy we are already at a disadvantage because of this built-in "fact" base that Republican propagandists have been working on in subtle and unsubtle ways for decades.
The "weaknesses" of our side that we most need to combat are mainly fake weaknesses that corporatist propaganda has instilled in them, rather than the minor real weaknesses (which do exist, but are much less frequently talked about by either us or our opponents on the right). So we somehow need to not only make the argument that single-payer or the public option is better than what we have, but we also need to debunk a lot of nonsense. That's hard to do succinctly.
2. The fact that a lot of Rethug ideologues are seemingly impervious to reason.
I've had this discussion on healthcare many times with Republican relatives, and many times I thought we were having a reasonable conversation and I was getting through to them. Then, the next time I talked to them, they were back to spewing the SAME debunked talking points that I carefully explained were false the last time. I don't know why this is (maybe it's just that they spend a lot more time watching Fox News than listening to me), but it often seems to be the case. I think part of this is simply caused by the authoritarian worldview, where thoughts and ideas are carefully compartmentalized and insulated from one another. Authoritarians don't let new information sink in if it threatens their existing ideology.
3. The fact that many people genuinely aren't aware of the true horrors of our "insurance"-driven system.
If you haven't had a major illness, chronic disease, or been without cushy employer-based insurance in your life, it's going to be harder to get you to understand why our current system is such a problem. I can't tell you how many times I've had to explain to this sort of person that a) not everyone is healthy and holding a good job that pays for most of their insurance costs for them as a benefit, and b) that they aren't paying for the true costs themselves (many don't even understand that their employer is paying part, or most!). Rethugs are already often more impervious to empathy, so this is especially problematic if they haven't experienced it themselves. I've seen many a flip-flop on this issue when someone experiences a health crisis and realizes how much it costs out-of-pocket. This issue can be helped by recounting personal stories, especially from PEOPLE LIKE THEM. Don't let them get away with the lazy, self-serving thinking that the only people who have problems getting healthcare are the lazy, the poor, or the irresponsible.
4. The fact that healthcare policy issues are extremely complex, nuanced, and subtle.
For normal people, who don't read about healthcare policy every day, it can be very difficult to even understand the problems, much less evaluate the relative merit of potential solutions. Unless you've spent a lot of time reading about the issue, you might not be aware of a lot of the real causes of our healthcare crisis. Again, getting into all those sorts of nitty-gritty details is not a strong point for Rethugs, and they tend to ignore them and just go with what whomever they trust the most tells them/what feels right/what confirms their biases about how the world works, etc. It's just easier that way.
5. Somewhat related, the fact that healthcare is a very fractured, multi-faceted problem.
I see tons of letters to the editors written by people who think they know "the" solution to our healthcare problems because they have identified one thing (malpractice lawsuits is a popular one for Rethugs; another is illegal immigration) that they think is the cause of the high costs we're all having to pay. In reality, while there may be some merit to some of these arguments, there is no one solution to reducing healthcare costs. There are many contributors to our high healthcare costs, and they are all interrelated. To this end, I usually argue that single-payer would be the best way to create a mechanism to address all the other, more minor, problems once we address the insurance issue.