Your principle of “Look before you leap” seems like an appeal to inductive reasoning or to some other basic notion of prudence that contrasts only with sheer insanity. So you mean to identify conservatism with sanity or with elementary intelligence or vitality. That’s the fallacy of equivocation I criticize in my article on Oakeshott (link below).
“Look before you leap” means we should act based on our experience. As I say in my Oakeshott article, we’re all conservative in that sense (as are all animal species), so that sense can’t be decisive for the political question of how conservatives differ from liberals. If your pragmatic conservatism amounts to some such equivocation, that’s a problem.
I agree that technological change matters a lot, and that the postindustrial billionaires can be compared to the medieval landlords. But obviously what’s modern and humanistic about the industrialists is that they operated in the social context of capitalism rather than feudalism. The medieval societies were caste-based, whereas capitalism is supposed to be open-ended, allowing for upward mobility in defiance of the traditionalists’/conservatives’ patriarchal and racist prejudices. Technological progress and capitalistic creativity were supposed to increase the living standards of the majority, creating a middle class that would be worthy of democratic control over the affairs of government.
Theoretically, the medieval folks could have changed their mindset at any time. That’s what the humanistic Renaissance was. Changing their mindset would have led to political and economic revolutions, so the peasants would have deemed themselves inherently as valuable as the nobles, in that both classes were made up only of human persons. As a result, the peasants would have insisted on human rights, such as a proper education, and they’d have refused to be treated as serfs or as servants of the upper class. They’d work to create an economy of abundance to honour their common humanity. Again, that’s what happened with the revolutions of modernity, and the humanism ramified through all areas of society. Conservative Christendom is what kept them down by enslaving their minds.
So I’m pretty sure I’m on sturdy ground there. But again, as I say in these articles, I’d distinguish between the intentions and the effects of modernity. Liberals tend to agree with the intentions of capitalism, for example, whereas conservatives agree with the (monopolistic and plutocratic) unintended effects.
