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.

Sorry, but "an escalating cycle of rebellion and repression" doesn't come under my definition of "stability." It may come under a President's definition of "stable until I'm out of office," but that's another story.

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.

Unfortunately, the historical norm is for a tyrant to be replace by another one. People don't appreciate what a historical freak democracy is until they actually sit down and make a list over all the societies of the past few thousand years. Even the U.S. itself is partly a matter of luck, and hundreds of years of English history, and even then it was touch and go. Cripes, it was only in my own lifetime that all Americans finally got real equal protection under the law.

I've been giving this a lot of thought lately, and while I won't go into it here, the facts of history seem to show that the "need for freedom" that is one of the foundations of idealistic thinking may be something else entirely. Maybe I'll try to assemble this sometime into some coherent form and put it into another post. It's possible it meshes in some way with the thinking you've been doing and reading about.

In the context of this post, it means that yes, a society that values individual rights DOES have to be forced into existence in many cases. If nothing else, you'd have to concede that based on historical evidence authoritarianism does seem to be the human species' ground state. If all it took was time to "mature," God knows humanity has had plenty of time. There's got to be more to it. And yet, societies DO manage it, it seems to result in good things for the species compared to tyranny, and it seems it can even be stable. Go figure.

I have an evolutionary theory for this contradiction that you've heard before--crossing tribal apes with an intelligent reasoning brain is anything but a smooth fit. The entire human species is a kludge--a panda's thumb. So a society of individual rights and human beings may always be the equivalent of a bear riding a unicycle. I wonder what Ayn Rand would have come up with after being locked away with Jane Goodall for a year or so.

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.

I think this is right, but you can't leave force out of the equation either. We moved nations into democracy after WWII by essentially taking them over completely, sometimes for years. More than one person has pointed out that this may have worked a lot better in Iraq than the "Iraqis will naturally fall into democracy" theory did. But you'd have to also note that the occupations of Japan and Germany were done in an environment of absolute superiority with most of the rest of the world in wreckage. Does anyone really think we could have pulled off a Japan-style seven-year occupation on a single nation surrounded by many other hostile national powers untouched by conflict? Even if we'd had the resources?

"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.

You've got a point there. You sound like Jerry Pournelle, who's always saying "Republic, not an empire." The problem is that this choice isn't "binary" either. Too many people treat this issue as though the choice was "American hegemony" or "no hegemony." Certainly this wasn't true during the Cold War, and I don't think it's true now, either. Or as the PNAC put it in their paper, written in 2000:

At present the United States faces no global rival. America’s grand strategy should aim to preserve and extend this advantageous position as far into the future as possible. There are, however, potentially powerful states dissatisfied with the current situation and eager to change it, if they can, in directions that endanger the relatively peaceful, prosperous and free condition the world enjoys today. Up to now, they have been deterred from doing so by the capability and global presence of American military power. But, as that power declines, relatively and absolutely, the happy conditions that follow from it will be inevitably undermined.

I don't think most people realize how American (or to be more charitable, Western) military force has been responsible for preserving what little democracy there has been in the world over the past century. If humanity's ground state were democracy, we could get away with isolationism. Is it?