No, the key is eliminating the monopolies and protections that allow price manipulation by the big players in the medical field. Allow insurance policy sales across state lines, to create competition between insurance companies, allow competition in drugs (or at least allow the re-importation and re-sale of the cheap drugs the rest of the world gets from the US. Allow buyers and insurance companies to decide what a policy will cover. Then prices will come down, people will be able to afford both insurance and medical care, and charitable groups will be able to afford to help those that still can’t afford it.
With a strictly free-market system, a hardworking, self-employed person with a pre-existing condition won't be able to buy insurance even if it is opened up across state lines. I don't see anything in your proposals that won't leave that hard working, self-employed person still stuck with getting less health care than your typical illegal alien or welfare leech.
Sure, charitable groups could help, if you want to turn people into beggars, pleading for mercy from charitable groups.