I was exaggerating a bit simply to get a handle on where Libertarianism really rests with people. It seems like the hardliners really don't represent your average libertarian. Most libertarians I've spoken to aren't anarchocapitalists, they seem to be fine with a more moderate libertarianism, just as I'm fine with a more moderate collectivism. I don't want every market federalized, just a few things like medicine. Most libertarians don't want everything privatized, just a few things like Social Security.
If I may, though, not everyone has the opportunity to pull themselves up by their bootstraps. While I'm totally certain that you worked hard to get where you are, had a few small circumstances been different for you it's entirely possible that you might not be as successful. Had it not been for a shining recommendation from a professor, I wouldn't have landed my first job out of college. Did I earn the respect of the teacher with hard work? Sure. Did she have to write the letter? No, that was luck. I'm sure if you look back over your life, you might find a similar circumstance. It doesn't make you any less deserving of that which you've earned, but it should point out that not everyone has that one moment go right for them. Some people work just as hard as you or I, just as smart, but they can't reach their potential due to circumstances outside of their control. Because of that very real fluke, and because humans are a species that developed a sense of community and empathy, it's not wrong to help these people as a society.
That hypothetical homeless man may have, at one time, been giving 100% on the road for a bright future, only to get tripped up by circumstance and have the floor give out beneath him. Maybe he was sued and lost everything. Maybe he lost his job and couldn't find another one. Shoot, maybe he was born with a learning disorder and never had a chance to begin with.
When I see a homeless person, I like to think of him or her as a friend. I like to think of everyone as a friend. If a friend of mine was on the street starving, I'd want more than anything to help out. If a friend of mine was addicted to alcohol, I'd want more than anything to help out (without becoming codependent, of course).
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