If you look at the founders’ documents and writings on the subject, “well regulated” isn’t about “regulations,” but about the “proper functioning thereof, as the parent said. There is plenty written about the right to bear arms from that time period by those that wrote the constitution. Words do mean things and those meanings can’t be interpreted without historical context. The purpose of the 2nd Amendment is to protect against a tyrannical government — it’s illogical that the regulation by a potential tyrannical government was intended by the Constitution; it’s the fox regulating the henhouse.
How does a paramilitary organization "properly function" without regulations?
There's obviously a middle ground where regulation is allowed. There's no world where artillery, or arming the insane isn't acceptable in a civilized society. Conversely, the overreach of prohibition of arms in places like DC or NYC is not in alignment with the ideals of nation.
To me, the notion of armed civil insurrection against a modern state apparatus is absurd, and has been since the late 19th century. Civil disobedience and disruptive protest, including protest that undermines control of the armed forces, is the only check on the state's ability to wield force. Even a 3rd rate army is able to control civil unrest.