TL;DR:
First step to getting healthy: forget about free stuff!
It's hard work to get your life together, and it's understandable that we avoid it. What we find out sooner or later is that our suffering only increases the longer we avoid this challenge. And no one can do it for you, regardless of anyone's opinion about the matter.
You will almost certainly will need to ask for help, but it's in your best interest to assume full responsibility for your life... despite the fact that much of it is beyond your control!
Full answer:
I think this question is not based in reality.
Regardless of whether we think healthcare should be free, the reality is that it can't be free. Medical treatment requires time, energy, and resources. To say "I want free healthcare" is pure fantasy, and in the real world that would be saying "I want someone else to pay for my healthcare".
I don't mind sharing the expense on principle. But again, that ideal doesn't jibe well in a society where people (including myself!) have taken very poor care of their bodies, and insist that they are not responsible for that problem or its resolution.
Sure, the environment pulls for an unhealthy lifestyle. It can be far more difficult to live healthy than it is to live unhealthy when we're surrounded by advertisements that are designed to manipulate our emotions in order to have us make poor health choices, which provides profits to some corporate entity and its shareholders. And the unhealthy choice typically requires far less effort!
But by wallowing in self-pity and being averse to taking responsibility we only make it worse for ourselves. As my grandma used to say, "Life's a rattata and then you die." It's never been fair. It's a hard pill to swallow, trust me, I know. But like it or not, we have free will, and it is therefore impossible for any outside force to impose order upon our lives.
One could debate the philosophical merits of that argument, but practically speaking we go about our daily lives as if humans have free will. I'm only interested in discussions that can directly improve the quality of our lives. To that end I say that we must get our own house in order or live in chaos, plain and simple.
And that's important because with something like Obamacare, we are essentially asking the government to be responsible for our health. It's completely inappropriate. What we've really accomplished is to give up our right to choose whether we participate in the healthcare system, which goes against the very principle of individual liberty. It's progress, alright, but not towards a free Republic.
Disclaimer: none of this is meant as an atrack on you or your position, and I've tried to remain respectful despite my very different perspective!
Okay - I can respect that viewpoint and I get where you're coming from, but, using that perspective, how exactly is one expected to take responsibility for - and by extension pony up the capitalist-inflated life-ruining bill for - something that they were born with, or acquired over time because of a genetic factor, or caught from someone due to the actions of that other person? How is one expected to foot the massive medical bills that come from genetically-induced cancer, or afford drugs and treatments that the local "pharma bro" or big CEO can make 5,000% more expensive at the drop of a hat?
When we talk about healthcare solutions, we are primarily not talking about people who make poor decisions and don't take care of themselves. We're not even talking about people who are influenced by external factors, like those malicious and irresponsible advertisements you mentioned. We should be talking about them as well, because it actually becomes incredibly difficult at a micro level to take two people and say one deserves assistance and one doesn't based on certain actions - but we're really not. We're more or less talking about people who absolutely cannot be expected to take full responsibility for what has happened to them or for their state of being. We're talking about people systemically disenfranchised financially, to the point that "hard work" cannot and will not elevate their socio-economic class; we're talking about people who may never have done anything wrong but now have cancer, or HIV, or chronic pain, or MS, or ALS, or any other number of things over which they have absolutely no control. Things as simple as accidents, or the flu, or opportunistic infections, or sporting injuries.
But the idea of the systemically disenfranchised who can't just take responsibility for their situation and change it themselves are the people who take center stage here; the United States is no longer (and has probably never been) a place where one knows they can change their lot in life, as income inequality is too high and social mobility is too low.
If medical bills were affordable in the first place, then maybe your perspective would make more sense to me, but I just can't fathom the concept when we live in a society in which it costs thousands of dollars simply to step into an emergency room and say "help, I'm dying." It's hard to say we should all be our own keepers and "get our house in order," as you put it, when it can cost hundreds of thousands or millions of dollars to stay alive because of something that happened entirely randomly, or happened because you were a victim of a crime or freak accident your insurance (if you have it) won't pay for or this or that, you know? For a lot of people, that's simply not possible.
There's a lot of rhetoric built around the choice element you mentioned, but that oversimplifies the concept of freedom and individual liberty. We shouldn't have to worry about the choice of whether or not to participate in the healthcare system, and we shouldn't have to worry about choosing this insurance provider or that treatment center or the slightly different generic pill over the branded one.
Maybe I'm alone in this thought, but health care should exist as a separate entity from our wallets, our private sectors, and the goods and services that we exchange for prosperity. It's literally needed to live - in modern society, it's becoming as basic a function as fire departments, police units (though their effectiveness is another debate), legislative bodies, and more. It's something that should be by and large paid for through taxes and the concept of the social contract. In order to be a part of a functioning, prosperous, and peaceful society, one of the things that we should be willing to exchange is a part of that prosperity for the guaranteed wellbeing of our fellow citizens. This is how we treat things like the military and the protection of the land we occupy, so why is it not the way we treat the protection of the bodies we live in?
That some people make terrible decisions and don't keep themselves healthy shouldn't mean another should die because he or she can't afford insurance and then, by extension, can't afford medication or treatment. There's a reason so many other nations have moved to a better, more affordable, and universally covered model: we know, by virtue of statistics and data and other assessments, that it works, and it's probably scalable to a large nation like ours.
My apologies if any of this is hard to understand or seems more "angry" than intended; I tend to ramble a little bit and get lost in the passion of the moment, but I find that I make more sense when I get all my words out! {XD} The only entity I'm at all frustrated with is "the system," as cliche as that sounds.