Certain texts are of interest in Yves R. Simon, Freedom and Community, ed. Charles P. O’Donnell (New York: Fordham University Press, 1968). Upon second glance, the tone of the potentially relevant essays is only of secondary interest (though they are not without their applicability, albeit remotely). If so inclined, see in particular “Liberty and Authority,” “Freedom and Community,” and “Autonomy and Authority.” In any case, given the overall concern with political-philosophical questions, which often contemporarily deal with the basic issue of individual and society, the thematic treatment of institutional subsidiarity gets somewhat placed in the background.
Another theme of interest here are comments that Simon makes elsewhere, sane remarks doubtlessly made by others, though with great clarity. (I believe an example text can be found in The Definition of Moral Virtue.) The great deceit of the “nature vs. culture” dichotomy is that we are led to think that the “natural man” (or, “the human person in a natural state”) is actually that which is most natural to the human person. In fact, human nature only comes to its fullest development in society. Here, your intuition regarding one’s idea of freedom is quite appropriate. If one considers freedom primarily as indetermination, one is trapped either in absolute voluntarism or in the pessimism of a kind of Epicurean theory of freedom that searches for a non-deterministic escape from the determinism of causes through some artifice (like the atomic swerve)—ultimately, I’ve always thought that such positions must end up in some kind of pan-voluntarism like that of Schopenhauer. In any case, one is in a very different situation is one imagines freedom in terms of the natural super-determination of the will to the good as such (in the order of nature) and to God in His inner mystery (in the order of grace by charity). Thus, our freedom of choice comes from the “overdetermined” nature of our will in comparison with all of reality. In that case, law becomes the rational expression of a particular ordering of this freedom. True law expresses the ways and means for freedom to be be free we could say.
Here, we see that the law vs. freedom dialectic, which plagues much moral theology on this matter following the probabilist debates, is deceptive. The moral law is “binding”, but it is experienced as such only because of our fallen tendencies. (There are some very lucid points said in this regard in Maritain’s Neuf leçons, which we should include if you make this point.) In any case, the debates came to center on when the “law holds” and when “freedom holds.” Thus, moral casuistry became concerned with when a given precept binds and when one had freedom of choice. (Thus, there were various positions staked out around the axes of “safety” (tutus) and probability.) I can provide you with some references here. Recent studies include:
Julia Fleming , Defending Probabilism: The Moral Theology of Juan Caramuel
Stefania Tutino, Uncertainty in Post-Reformation Catholicism: A History of Probabilism
Rudolf Schuessler, The Debate on Probable Opinions in the Scholastic Tradition
I have the first, the library at BCS has the second, and we’ll perhaps get the third when it is released. (Brill texts are expensive… Though, this volume looks like it could be quite good if done well.) Fleming and Tutino do not come at things the same as I do of course. I would also recommend, albeit in French, the famous articles by Th. Deman, OP on these matters.
In any case, those details won’t be necessary for us. It is most important to note this general problem in the background, namely that law is seen as being binding, something that distorts one’s understanding of law itself! Here, I agree with Pinckaers. (I do not, however, agree with his carte-blanche approach to critiquing all the Thomists before him. There is a haughtiness to his generation, as though they will reinvent theology themselves on their own terms.) That being said, his text here is admirable and important. I also recommend for understanding freedom in a sane way:
Yves Simon, Freedom of Choice
The relevant passages of Jacques Maritain, Bergsonnian Philosophy and Thomism (An excellent précis of the Garrigou-Lagrange text noted below)
Also, see Maritain’s essay “Freedom” in Existence and the Existent
Finally, more technical reflections on this matter can be found in Garrigou-Lagrange, God: His Existence and His Nature, vol. 2
In any case, we thus come back to the issue of nature and culture noted above, for this same issue is found on the axes of freedom and law. Just as nature is most truly natural in culture, so too freedom is most truly free in the context of law, provided that law is understood as a right ordering of practical reasoning for the structuring of that reasoning in terms of the common good (which integrally contains the flourishing of the social being that is the human person). Freedom is not free in absolute autonomy but precisely as being actualized in line with the deep élan that animates as being ordered to the search of that which is good in itself.
To this end, I am still finding it difficult to track down the quote I’m thinking of in Simon’s The Definition of Moral Virtue, but there are very relevant points made in the first chapter, much in parallel to the fundamental intuitions of Pinckaers.
Doubtless, certain points of interest can be found to this end in Adler’s lengthy study from the 1950s. We likely won’t have time to incorporate that.
Also, for some thoughts on authority and representation (which is philosophically important for articulating these matters—though, I’m trusting that you’re also looking into the various necessary historical sources patristically, given some of the texts you have cited), see Simon’s treatment of this in The Philosophy of Democratic Government, "Authority in Democracy" in https://maritain.nd.edu/jmc/etext/pdg.htm. In particular, see the discussions directly related to the papacy in “The Transmission Theory” (https://maritain.nd.edu/jmc/etext/pdg-3d.htm). I can get you pagination when you have citations.