So, while I agree we are never free from hypothesis as long as we are in discursive mode, I think we can be free in non-discursive modes. This freedom may not be of much use for discursive philosophy, but it certainly has its role in the arts and in self-cultivation. — Janus

Yes. Good point. Within the realm of opinion there are some that are better to hold than others. Some desires and goals that are higher than others.

What could the value of metaphysical speculation consist in if not to show us that metaphysics is undecidable, and not a matter of reaching some theorem which is guaranteed to be correct by rigorously following the rules?

I think this would be radically underselling it. Consider the image of the soul—the charioteer of reason training the two horses (the appetites and passions)—in the Phaedrus. It is the image of the divine that gives the charioteer the wherewithall to break the black horse of the appetites and train both horses so that the soul functions as a unified entity, rather then there being a "civil war within the soul," (the phrasing of the Republic). So what is at stake is ultimately the freedom of the human person, since it is reason, and its ecstatic nature, that allows us to go beyond current beliefs and desires in search of what is "truly good," not just what is said to be good or appears to be good. As Socrates says at like 510D (IIRC), everyone wants what is truly good and despises opinion in these matters (reality vs appearance).

So it's absolutely true that we don't know this sort of thing the way we know "the Declaration of Independence was signed in 1776," and we can't learn it in the same way, e.g. simply reading it somewhere. But it's not just nescience or awareness of nescience that is at stake. The whole person is ultimately transformed, reason, the most divine part of the soul (e.g. the Timaeus, the "golden thread" of the Laws) reaching down and coloring the lower parts.

This is why Plato also has Socrates speak of erotic desire for the Good (the desire to "couple" with it) and spirited love for it. It's a full reorientation of all parts of the person, which is ultimately what allows us to be self-governing and self-determing, and thus ultimately (more) fully real as ourselves. For a counter example, a rock is "less real as itself," because it is essentially just a bundle of external causes, not self-generating in any way. Plato doesn't think rocks are unreal, something along the lines of Shankara, but he does have a conception of vertical reality. The orientation towards the Good is what makes us more real as ourselves, and so this is why there is good reason for us to think it is as at least as "real" as us when we are actualized.

Also to consider here is the image of Socrates as a midwife and the idea of "giving birth in beauty," in the Symposium and the generosity of the creator in the Timaeus. Giving birth in beauty, an attitude of love, is also a key element of the perfection of freedom, and thus full reality. The ecstasis of knowing, and the identity of the self with the other in love, has a transcedent role in bringing a person beyond what they are, which is ultimately the nature of freedom in the classical tradition (i.e., the ability to do the good, rather than the potential to "do anything," act versus potency).

So, while I agree we are never free from hypothesis as long as we are in discursive mode, I think we can be free in non-discursive modes. This freedom may not be of much use for discursive philosophy, but it certainly has its role in the arts and in self-cultivation.

:up:

Letter VII might be the most clear on this. The type of knowing associated with language and demonstration is not, ultimately, the sort of union with what is known that is needed for that which is "good in itself," since discursive reasoning always involves the relative and relational. Aristotle (Metaphysics X IIRC) makes a somewhat similar distinction between two types of knowledge. First, there is the sort of propositional knowledge that combines, divided, and concatenates, which has falsity as its opposite. Then there is awareness of undivided wholes, which can be more or less full. The opposite of this second sort of knowing is ignorance, not falsity. There is a key distinction between Plato and Aristotle though in that Plato often talks about the knower going outside of himself in knowing, whereas Aristotle talks about the mind becoming like things known, i.e. more external vs internal language.

Plato cannot answer this question with mere words, which are relational and thus always point to relative goods — Count Timothy von Icarus

The same point has been made about terms such as reason, from the Latin ratio. It is a comparison of one thing to another. If the Good is singular then it cannot be grasped by comparison. At best what you have is a likeness - the Good is like this or not like that.

Plato then, sees philosophy as a transformational process. — Count Timothy von Icarus

I think he sees philosophy as a type of poiesis. Myths and images are a part of this process. Socrates proposes banning the poets from the just city, but this is not to ban poetry. The philosophers are the poets, the image makers, the puppet-makers whose images cast their shadows on the cave wall.

I think this is one way in which Plato and Wittgenstein differ. Wittgenstein is not a maker of images of a transcendent reality. Perhaps he thought there were already enough of those.

Anyhow, here is an interesting contrast of the two that brings up Wittgenstein's interest in Schopenhauer as well. It mostly focuses on the Tractatus though.

https://ibb.co/ZWBMH8V