The most important example of contemporaneous (with the 2ndA) usage of "well regulated" is found in
The Federalist 29, written by Hamilton and focusing on the Constitution's militia clauses where the actual regulation of the militia would be authorized. This excerpt speaks expressly and directly to the concept of "well-regulated militia" and what that designation means and what the repercussions would be of a demand that "all the militia"
actually be, "well regulated."
"The project of disciplining all the militia of the United States is as futile as it would be injurious, if it were capable of being carried into execution. A tolerable expertness in military movements is a business that requires time and practice. It is not a day, or even a week, that will suffice for the attainment of it. To oblige the great body of the yeomanry, and of the other classes of the citizens, to be under arms for the purpose of going through military exercises and evolutions, as often as might be necessary to acquire the degree of perfection which would entitle them to the character of a well-regulated militia, would be a real grievance to the people, and a serious public inconvenience and loss. It would form an annual deduction from the productive labor of the country, to an amount which, calculating upon the present numbers of the people, would not fall far short of the whole expense of the civil establishments of all the States. To attempt a thing which would abridge the mass of labor and industry to so considerable an extent, would be unwise: and the experiment, if made, could not succeed, because it would not long be endured. Little more can reasonably be aimed at, with respect to the people at large, than to have them properly armed and equipped; and in order to see that this be not neglected, it will be necessary to assemble them once or twice in the course of a year."
Let's scrutinize this from top to bottom . . .
From the start it is clear that "the project of disciplining" has more to do with -
practice makes perfect-than
-Congress shall have the power to regulate-. "Expertness in movements" is not something the militia can achieve by having a parchment sent from Washington DC read to them, it "is a business that requires time and practice".
The "yeomanry" was a familiar term describing the class of English subjects who were liable to serve in British militia. Hamilton's adding of, "
and of the other classes of citizens" is a direct refutation and condemnation of the exclusions outlined in English common law and their bill of rights that the framers held in contempt. That general inclusion,
-of every class of citizen-, without regard for land ownership, religion or title, told the people that
no exclusions or qualifications attached to a citizen's status were to be enacted or inferred onto arms keeping and bearing by the proposed constitution.
Again, "well regulated" used to describe militia is merely an accolade; it describes a quality; ("
the character of") the unit and the men. That description is
earned. It is earned only after extensive "military exercises and evolutions" and demonstrating expertness in military readiness and order ("
acquire the degree of perfection"). It is a description that is
bestowed ("
entitle them to"), it certainly is
not describing the legally constrained condition of simply being
under regulations that you are claiming.