I agree that there’s some wisdom in democracy, in that way of dealing with the tendency for power to corrupt the rulers. As the ancient Greeks knew, democracy has its drawbacks, too, such as demagoguery and the tyranny of the majority (as in group think, etc).
In so far as “conservatives” support democracy, conservatism isn’t just a cynical con. Alas, democracy is inherently liberal and progressive, in the big picture. So conservatives have no right at all to democratic wisdom.
Where conservatism enters the picture in George Will’s account is in the economic sphere, in Will’s “Darwinian” celebration of laissez-faire capitalism. When you speak of the “fluidity of the elites” in the Founders’ vision for the United States, that mechanism of voting has no bearing on the private sector—unless you think that the freedom to buy and to sell tends not to create monopolies (the economic equivalent of monarchies) via the law of oligarchy and so forth. The New Deal was a political rectification of the conservative/monarchical/autocratic end point of pure capitalism.
I agree that the Founders allowed for political self-correction and for a learning process to create “a more perfect union.” But that’s precisely why the Founders were progressives rather than conservatives, and why the nondogmatic, amendable Constitution is likewise the opposite of conservative.
George Will doesn’t “say” that nature saves us. His libertarian conception of capitalism implies it, as does the monarchist’s appeal to the divine right to rule, which sanctifies dominance hierarchies (as in God’s tyranny over Creation, and thus the king’s right to tyrannize the peasants).
You can call yourself a conservative if you want, of course, but if your conservatism is consistent with the New Deal, I think you’ll have a hard time distinguishing that conservatism from liberalism. That’s precisely the purpose of Will’s book, and in through the back door slipped Old World conservatism via the libertarian’s idolizing of the free market which leads to plutocracy, to a late-modern form of autocracy.
The distinction between planned and unplanned/wild societies is meant to get at the big picture, at the contrast between intelligently designed societies and ones in which nature takes the wheel. Liberals/modernists prefer the former, and conservatives and “libertarians” implicitly prefer the latter.