yossarian, I know you're not mainly talking about Trump, but in saying that his ineptness is crippling the response to authoritarian government, I think you're omitting a pertinent fact. When we're talking about the state of world democracy and 'freedom' we need to look at the trouble areas. Sure, there's Russia, China, and some others. Africa - hey, no one cares, right? And then there's the Mid-East. The Balkans have historically had tons of conflict, which did make it into Western affairs briefly during Clinton's term. But it seems to me that much of the socialist/dictator/democracy strife has been fueled not by some kind of local sentiment of 'feeling about' open societies, but rather has been dictated by the world superpowers. The Mid-East situation such as we now know it was essentially begun by the English in how they carved up the territories. It was perpetuated by the U.S. and Russia trying to divvy up who would collect what in that region, and most especially affecting Persia/Iran, Saudi Arabia, and Syria as far as large hegemony is concerned. It wasn't some trend towards open or authoritarian society affecting these changes, but rather buckling under pressure from big oil interests and CIA regime change plots. Trump may be seen by some as a buffoon, but he hasn't invaded anyone or toppled any governments that I know of. That's the first time I can say that of a President since...what, the 90's? So in weighing what Trump may be contributing to the situation, we must also look at what he didn't do, such as destroy Libya.
But to be honest I think there are technological issues in play that go beyond the current state of a country or two going towards authoritarianism. Part of it, as you say, is the fact of mass surveillance, and how once this technology exists you can't close Pandora's box. The same will be true of genetic engineering as some point, and of AI as well. That some governments become more paranoid and controlling is probably an inevitable result of communications technology developing as it has; they have more chaos to contend with now, but also have to contend with actual intelligence operations that use 'public' infrastructure. And of course the disinformation wars are at an all-time peak (and probably getting worse), where the capacity for a regular citizen to hear a piece of news and know whether it's true or not is quickly approaching zero. Once deep fakes becomes more advanced I doubt we'll be able to tell whether footage is legit or not.
And I mean, when talking about representative government, the main drive toward it would be that people see how attractive and functional it is, right? Except that the U.S. in particular demonstrates in many ways how ineffective it is, having more restrictions than the Chinese systems and yet potentially also fewer advantages. Leading by example would surely require doing something about the inherently corrupt money-politics system in place, which by comparison makes an autocratic dictatorship look good in some respects if at least they're doing all kinds of infrastructure improvements for their society.