How do (the more reasonable) libertarians approach classic market failures? The free market is great when conditions for a free market are met, but all too often that isn’t the case. For example, what would a libertarian say about cable companies or airlines merging to form a natural monopoly or oligopoly or similar anticompetitive practices. Likewise what does a libertarian approach to healthcare look like in our setting of consolidating insurance companies and hospital systems, once again for the purposes or limiting competition.
As I alluded to earlier, I think excessive faith in a completely unregulated totally free market is the chief weakness of the party. Regulations I believe in that many libertarians don't include things like a livable minimum wage, strong anti-trust / anti-monopoly laws, strong environmental protections, building codes, workplace safety regulations, etc. It's pretty clear that pure unrestrained capitalism gives us robber barons and serfs with fewer than 10 fingers.
As for healthcare ... obviously it isn't a simple problem that can be solved or even adequately described in a few sentences.
Obamacare is a miserable failure in large part because it upended an insurance market that was only barely functional in the first place by applying a bunch of extra rules and conditions that defy 3rd grade math concepts. But the root of its failure is that we're still working with a system that thinks "insurance" is the right word/system to apply to a service
1) that everyone should use every year (for preventive treatment), and
2) that everyone will almost certainly use at some point in their lives (for non-preventive treatment), and
3) for which people who need it once will almost certainly need much more of it
"Insurance" is a concept that is properly applied to a potential need that is unpredictable, with a low risk of occurrence, but high expense when it does occur. That's not healthcare. Having health insurance companies at all is kind of an ass backwards way manage the money in this kind of system.
My opinion on the whole thing has changed over time, but on this particular Friday, I think the best answer is taxpayer funded care for everyone, with hard caps (yes, death panels!!! oooh!!!). Given that, I'm on board with the libertarian ideal of a free and minimally regulated market for individuals to pay cash for what they need or want sooner or under different conditions of their choosing, and/or purchase actual insurance for needs or wants that exceed the public system caps.