I think the difference in worldview comes down to a difference of thinking about healthcare as a commodity like any other good or service, versus as a basic human right.
There is a major issue with defining "health care" as a human right. To see where the objection lies, consider other rights.
Freedom of speech does not compel anyone else to do anything on my behalf. My freedom of speech is not a mandate they have to carry out, but a prohibition on what they cannot do to me. Conversely, it also forces me to observe the exact same prohibition when others have something to say. The same can be said about the freedom of assembly, the freedom to associate, as well as property rights. All of those things (1) are prohibitions, so they do not force anyone to do anything and (2) are strictly symmetrical in the sense that I ask of others no more and no less than I am myself forced to respect.
Now comes healthcare. As much as we all understand the importance of healthcare, it is not free. Your right to healthcare services is effectively a right to the labor of someone else. And that's where conservatives disagree. By the way, as I pointed out many times, the government is not the only way to organize people to tackle social problems such as deaing with health issues among the poor. It's not because conservatives do not like the compulsory program that they would not applaud voluntary efforts. Everyone agrees that a child born to poor parents receiving a bad diagnosis is a sad part of life. Nobody would just say "tough luck."
I don't think of healthcare as a human right, specifically because of the aforementionned reason. On the other hand, I don't think of healthcare programs as peculiarly problematic. The only difference here seems that I am perfectly aware this requires digging into the pockets of other people by force, so I see that as a necessary evil, not as a right.
But the whole purpose of healthcare is to take care of sick people, not make money. This is not working out because the free market is not designed to address the problem we are trying to deal with here, which is to have a healthier society. These companies are working in a broken system. That is why it seems to me that healthcare, among all economic sectors, should be taken out of the free market system. This is one of the rare situations where the ends and purposes of what we as a society want and need, and what the free market wants to provide, are not aligned.
I'm not going to take issue with your commentary on healthcare and health insurance. There arguably are information problems involved that suggest it's not always to be dealt with effectively in a decentralized system, as much as I dislike the idea of centralizing decisions. I'm not an expert in health economics either.
On the other hand, I will absolutely take issue with how you personnify "society." It is a collection of individuals with different preferences and who likely will face different costs and benefits when policy changes are made. The core problem behind your personnification of society, of treating it as if it was proper to call it "we" is essentially the formal problem of coherently aggregating individual preferences. Here comes Arrow's Impossibility theorem. The idea is this: assuming that individuals have coherent preferences (meaning, it produces a proper ordering of relevant options), can we bundle them together and be certain that the resulting "social" preferences are also coherent?
If you impose that unanimity should be respected and that the social preferences cannot be the preferences of just one person (what we call the dictatorship condition), it's impossible to guarantee you will get a coherent set of preferences. That's why you get things like the Condorcet paradox, by the way. So, when you say "we" to mean society, it
necessarily either is (1) pure nonsense, or (2) you mean a small group of people imposing their preferences to others under the guise of social welfare. Society is not a person. It does not have interests. It does not have goals. Individuals do. What "you as a society needs" really means what a subset of the population wants to impose on another subset of the population.
I do not always object to the idea that it might nonetheless be desirable, but I don't try to lie about it. It's very clear that when I favor those types of policies, it does involve coercing some people for the benefit of others. That's how
all redistributive policies work. All of them without a single exception: it always forces some people to work for the benefit of others. I at least have the guts to not sugar coat it.
The free market is great. But it is not a magic cure-all that can just be blindly applied to all problems to fix them.
For the sake of clarity, I will add that I never said it should.