Democracy vs Dictatorship is a Meaningless Abstraction
Is it more likely that a democracy or a dictatorship would better serve the needs of the people?
Resist the urge to jump to waffling arguments, like "Benevolent dictatorship is the best form government, but suffers from the problem of succession." The question is a question of probability, and probability at its most fundamental is the counting of all relevant outcomes and possible outcomes, then taking the proportion relevant outcomes to possible outcomes.
What are the possible outcomes in this scenario? We would have to imagine every possible society past, present, future, and hypothetical, varying from:
tribes of Homo Erectus hunting with primitive spears;
brain-implant-wearing outworlders living on Dyson spheres;
post-apocalyptic scavengers scrounging for past technology at the feet of ancient metal towers, rendered as skeletons by a mythological blastwave
And we would have to consider all possible leaders who could arise under such circumstances, and thus what exact forms of popular representation or power concentration would arise. If, in thinking the scenarios I raised are irrelevant or absurd, we narrow our imagination to our own society, and then again to our preconceptions of our society, we have only succeeded in painting a bullseye around our arrow.
Nor do we need to resort to fiction describe societies very different from our own. Intellectually, we recognise that:
the United States is very different from Great Britain is very different from France is very different from Germany, is very different from Finland;
the Great Britain of today is very different than the British Empire upon which the sun never set, is very different from the United Kingdom whose monarch had not yet been subordinated by Parliament, is very different from England under the Plantagenet Dynasty which fought the Hundred Years War over its French claims, is very different from Roman backwater province of Britannia;
even within national borders a society is composed of smaller societies, divided by provincial administration or ideology or ethnicity, such that we would never mistake an Amish man for a Silicon Valley dudebro
But in practice, we can only see in clarity two societies: Our own society, as viewed from our own ethno- and socio-economic perspective, and America, as depicted with all the fury and nuance of social media. Thus the advantage of fiction is two-fold. Not only does it broaden our view of what is possible, its vividness frames our intellectual understanding, preventing it from collapsing into the simple structures we can at a moment remember.
(In the spirit of never offering a problem without attempting to offer a solution, my first pass attempt of identifying good leaders without worrying too much about the specifics democracy or dictatorship is that they would be 1) highly educated, 2) have experienced personal hardship, and 3) driven by rationality, willing to admit mistakes on the basis of evidence, and also be willing to confront other people based on what they reason is true. Basically I'm just thinking of Lee Kuan Yew 😂)