If you are talking about health insurance, that is a big mess in the US. The problem with healthcare in general is that the biggest customers are either chronically ill or dying. Also, in emergency medicine, there is an ethical mandate to treat first. It's not practical or ethical for a healthcare provider to secure means of payment in the middle of an emergency. Most times the indigent or underinsured end up not paying the bill. Therefore, the healthcare providers are forced to raise their prices and try to make up for it by charging more. It just ends up being a feedback loop where the amount the healthcare providers charge keeps rising. In my opinion, the healthcare market is going to end up being socialized no matter what system you try.
Is it practical or ethical to socialize all healthcare, and pay for it with socialised debts that can't be paid at some point in the future? It's easy to say "socialize it to simplify it" now, and forget about how everyone maintains that long term. But remember why we're here on bitcointalk: government debts all over the world have increased more since 2008 than they have since the year 1908. That means big expenses like socialized healthcare are gonna either end or get drastically cut the world over once the government debt market reverses trend.
I'm just saying, in the end, it becomes socialized in one form or another anyway. I work for an ambulance billing company. They are ethically and legally required to transport anybody. It would be totally unethical for us to leave a person untreated and untransported who is obviously having an emergency, even if the crew suspects the person does not have the means to pay. In the end, the ambulance service charges a higher price in order to recoup the costs from people who do have the means to pay. In the past, most hospitals were run by churches and non-profit corporations. Many still are. In the end, you just cannot have an effective free market when the main consumers happen to be chronically ill or dying.