What The Second Amendment Really Says:
The Second Amendment talks of "a well-regulated militia,..." not THE militia specifically, but A militia in general. Then it says, "...,being necessary to the security of a free state,...". Hmm, "a free state". Everywhere else in the Constitution where "a", "another", "any", "no", "each", "every", "(F)oreign", "new", "one", "other", "particular", "the", "that", "same", "such", or "the several" state(s) are addressed, it is clear that the political unit "state" is being addressed, except in Article II, Section 3, which I'll address later. These are demonstrative adjectives. In the Second Amendment, the adjective "free" modifies "state" and does not demonstrably indicate a political unit state, but a condition. Since there is no comma between "a" and "free", one of those adjectives is demonstrative("a"), and the other("free") a simple modifier of whatever "state" is.
So, we're talking about a free state. Is it talking about a free political unit or a free condition? If it said , " ...being necessary to the security of the several states", or "...,being necessary to a state", or, "...,being necessary to any state," it would be more in line with the remainder of the Constitution and undeniably talking about the political unit definition of "state".
The word "state" is also used as "condition" elsewhere in the Constitution - Article II, Section 3, which commands the president to report on the state of the union. Right there in the Constitution is precedent for the word "state" to be used with the meaning "condition", as well as the more common "political unit". Bear with me a little longer.
The Second Amendment says, "...,being necessary to the security of a free state,". OK. Cool! What about the security of the nation? Article I gives Congress power to call forth the militia, to arm it, and place whatever portion of it into the employ of the United States it deems necessary. Did our Founding Fathers forget all about that when they drafted the Second Amendment? Wouldn't they have covered that in the amendment by adding something like, "..., and to the security of a free United States,..."? That would have made it clear and without question that the amendment referred to the political unit definition of "state". I don't think they forgot about the security of the United States, do you?
I think they covered the security of the United States, and the several states, by casting a wide blanket with the "condition" definition of "state". Again, I'll remind you that the Second Amendment talks of A militia, and not THE militia. So, by not addressing THE militia, how could it be addressing a STATE, a specific political unit, when it talks of A militia, which is non-specific? The only correct grammatical context is for "state" to mean "condition" in the Second Amendment.
The concrete that has been cast as the foundation for this is the fact that the Second Amendment addresses a RIGHT of the PEOPLE . Security of the state be damned! This is about the security of the PEOPLE! We live in a free state(condition), not the state! Only something alive can be free. A state is a political construct, bound in servitude by the Constitution. It can't lift up its skirt and tip-toe through the tulips! We can - if we so desire to wear skirts - But, I digress. The point is, it's about us and how we live, how we maintain our freedom, and how we restricted those in government.
There has been a question raised about the capitalization of the word "state" in the Second Amendment, that it would indicate the use of the word to indicate the political unit. Well, if you scan the Constitution, you'll find that the Founding Fathers capitalized all nouns instead of todays practice of only capitalizing proper nouns. Both the political unit definition of "state" and the condition definition of "state" are nouns. It's a name for a political unit and a name for a condition. Ergo, capitalized by our Founding Fathers.