I know a few such people myself, and I don't even really know that many people. One category is people with issues from birth: one friend of mine has a congenital heart defect, which is well managed, but completely disqualifies him from buying health insurance on the open market as an individual. So he is basically forced, against his will, to work for a large corporation, so he can qualify for their group health plan. Note that this is due to something that happened before he was even born. To me, that's not how things should work in a country with real individual freedom and equality of opportunity.
You misunderstand individual freedom. Freedom, in the context of a "free nation", isn't freedom from consequences or risks (even those out of a person's control), it's freedom from the imposition of state-sponsored force. This is an important distinction. We all invite a little state-sponsored force into our lives (i.e. the persecution of violent crimes, the civil court system, etc). Your version of "freedom" actually requires state-sponsored force at a fairly low threshold: if someone can't pay for their own health insurance or medical bills you're going to force others to pay it for him. You're not asking for voluntary donations, you're taking with the threat of legal consequences. That can't be congruent with any meaningful definition of freedom.
It is you who misunderstands individual freedom. Freedom is not some formalist anarcho-capitalist construct, but meaningful ability to take individual action. That requires, as Hayek argues, that a functioning state exists, which provides basic physical safety, a minimum of economic security, and contract enforcement, within which people can act as individuals. Absent that, in the "state of nature", people are forced to cling to tribalist groupings (religions, extended families/clans, etc.) for security and coverage of the "risks common to all", which is not individual freedom but collectivism.
You're not really illuminating much by explaining with the contorted libertarian definitions of 'individual freedom'. Seriously, you can't think of a 'meaningful' definition of freedom that includes helping each other? Not necessasrily one you have to agree wtih, just one that is 'meaningful'?
