You present your thesis as a series of dualisms, and to my mind that illustrates the limits of viewing the world that way. Dualisms become paradoxes, often unnecessarily.

The first dualism, "I have seen both of these viewpoints in both Democratic and Republican leaders over the history of our country.", is explained, I think, by postulating that American Presidents responded to the realworld situation, if you'll forgive me, misrepresented in your second dualism, that, to paraphrase, tyrants either maintain stability or they promote dissension and radicalism.

In reality tyrants often have both effects simultaneously. They foster the conditions in which radicalism and dissent arise, but keep the lid on it, in an escalating cycle of rebellion and repression. In that light it's not so mysterious that Presidents have, for their part, approached both sides of the tyrant equation, supporting or undermining tyrants as seemed advantageous to America.

As you say, tyrants eventually die; and sometimes they reach the limit of their ability to maintain control through repression. When the tyrant's rule ends or collapses there's an opportunity to shift a society to democracy, because by definition the society is aligned to support change; when you've hit bottom, everything looks like an improvement. That is, the society is ready for the change; and in contrast we've seen that our attempts to force the situation by removing a tyrant ourselves have much less power to induce a change because the society has not come by itself to the stage where it can embrace the change.

The question of whether a culture is ready for democracy is an interesting one, though it's been tinged with a lot of partisanship and ideological rhetoric. I'm nearing the end of a literary Bataan Death March slogging through the turgid academic prose in a book titled "The First Idea" ("How Symbols, Language, And Intelligence Evolved From Our Primate Ancestors To Modern Humans") by Stanley Greenspan and Stuart Shanker. They're child development specialists, and what's interestingis that their premise begins with asserting that not only is emotion not the enemy of reason, but that human intelligence arises from emotion. They spend much of the first part of the book developing that thesis, and in the latter parts go further and hypothesize that both human evolution and the societies we've built in the latter stages of that evolution follow(ed) similar patterns of development as a human child follows. As far as evolution goes, it strikes me as like the old aphorism about embryology that "neoteny recapitulates phylogeny", taken to the next phase of development outside the womb.

I've coined an InstantAphorism™: "The brain is the embryo of the mind". Like it? Royalties may be paid through my PayPal account.

Through the lens of their framework, G & S show how societies may indeed be at different stages of intellectual development, just as humans can be individually at different stages of development. A society's level of cognitive development determines the kind of institutions it can support, and apropos our discussion, democracy requires a rather high level of intellectual development because it requires reflective thinking and a strong theory of the mind to allow people to coexist despite their differences.

Not every human society is there yet. If these ideas are correct, and they're highly plausible, we need to evaluate a society's level of development before we consider trying to take them to the next level. If they're not ready, we'll fail.

The corollary is to look for, as you say, a form of social organization appropriate to a society's level of development, at the upper end of the range, but within their range. It may define freedom differently than we do (and even Americans are divided on what freedom means), but the goal should be to improve their lot by promoting feasible instead of radical change. You can't skip necessary steps in human or social development.

As for "neoconservatives," I think they originally fell under the idealist "exporting democracy" line of thinking

Ummmm...no, too narrow, and overlooks the most striking feature of neocon (PNAC variety) thinking: American hegemony. Imposing democracy is one of the tactics they advocate, but what's important is that their goals are expansionist and, in a very real sense, represent a 21st Century reworking of imperialism. Hegemony is just imperialism on the cheap: All the benefits of power and control without the expense and mess of conquest and direct rule.