I don't have a catholic answer, but I have a few saints from the orthodox perspective that did go into this dangerous spiritual area. (That verse about removing the beam of wood from your eye before helping others seems to be of note here)
Short answer at the bottom. :)
St Isaac the Syrian. Isaac does not hesitate to affirm that the fallen angels are as much objects of God’s love and salvific will as are human sinners. We cannot speak about the one without speaking about the other. God loves the demons and desires their reconciliation:
Nor are we able to say that the love of the Creator is diminished towards those rational beings who have become demons as a result of their demonic action, and is any less than the fulness of love which He has towards those who remain in the angelic state; or that it is less for sinners than for those who are justly named righteous. This is because the divine Nature is not affected by what happens and by opposition, nor does there spring up within it any causal stirring which takes its origin from creation, and which is not to be found with Him from eternity; not does He have a kind of love which originates as a result of events which take place in time.
Rather, everyone has a single place in His purpose in the ranking of love, corresponding to the form He beheld in them before He created them and all the rest of created beings, that is, at the time before the eternal purpose for the delineation of the world was put into effect. For it was not with an adventitious love that He had, without any beginning, the stirring that initiated the establishment of the world. He has a single ranking of complete and impassible love towards everyone, and He has a single caring concern for those who have fallen, just as much as for those who have not fallen.
And it is clear that He does not abandon them the moment they fall, and that demons will not remain in their demonic state, and sinners will not remain in their sins; rather, He is going to bring them to a single equal state of perfection in relationship to His own Being—in a state in which the holy angels are now, in perfection of love and a passionless mind. He is going to bring them into that excellency of will, where it will not be as though they were curbed and not [free], or having stirrings from the Opponent then; rather, they will be in a state of excelling knowledge, with a mind made mature in the stirrings which partake of the divine outpouring which the blessed Creator is preparing in His grace; they will be perfected in love for Him, with a perfect mind which is above any aberration in all its stirrings. (Isaac of Nineveh (Isaac the Syrian): The Second Part, II.40.2-4)
St. Isaac basically makes an identical argument for demons and satan, as he does for the salvation of humanity. See here for that one.
The issue of course ... well he can be so confident because revelations was not included in the 7th century Syrian canon of the Bible, the Peshitta. Hence we can only speculate on how he might have interpreted the verses regarding how demons were cast into the sea of burning fire... (Rev 20:10)
One dimension of the Syrian’s interpretation of Holy Scripture: he does not remain at the surface level of meaning. The Scriptures are an icon of God. We cannot simply state the “plain” meaning of the Bible as if that were sufficient; we must penetrate through the text to the spiritual truths and realities the words intend.
Isaac was not a practitioner of the allegorical method that had been popularized by Origen—he stands in the Antiochene school of biblical exegesis—but like Origen he knew that the truth of Scripture could only be apprehended by moving through the biblical letter to God himself, or perhaps alternatively stated, by allowing God to reveal the deeper truths of his Word.
Another thing is that the verse (Revelation 20:10) cannot pose an insurmountable problem for St Isaac. He reads the Bible through a hermeneutic of love, the very love he finds portrayed in the crucified Christ and experiences in prayer.
So I think even the "lake of fire" could only be the purifying fire of Love.
Wacław Hryniewicz writes, commenting on the holy monk:
Sin and Gehenna will be ultimately abolished, although their end is a mystery surpassing human understanding. The final outcome of the history of the created world must correspond to the beauty of the beginning and to the goodness of God. If we suppose the truly eternal punishment of sinners and demons, this would mean that the creation of the world was an enormous failure and mistake. God is able to overcome, by His goodness and beauty, every evil, even the opposition of the devil himself. (The Challenge of our hope commenting on Universalism of salvation by St. Isaac the syrian)
While Origen is mentioned... he doesn't speak as resolutely as St. Isaac. He almost appears to hesitate. If you want to read more about that...
Orthodox theologian Sergius Bulgakov dared to declare the eschatological restoration of the unholy spirits. This is 20th century, so definitely not related to catholics much anymore... All quotes below (if any) are from Bulgakov's "Bride"
But to put it shortly it follows the same logic as St. Isaac even though apparently Bulgakov is supposedly unfamiliar with the info I presented above (St. Isaac, the 2nd part, etc)
Basically the logic goes like this for Bulgakov.
Demons are parasites on the material plane of existence. They are cast out of heaven and cannot obtain any type of "sustenance" from God. However, they get to believe that they have some kind of existence at all. This however will come to an end.
Insofar as unlimited freedom is without bottom or support, satanism is the infinite rebellion of malice and hatred. The pseudo-creative activity of evil is rooted in this emptiness, which determines the pose of the “prince of this world,” who pretends to be the absolute center of creation. For a time there exists the possibility of such an illusion here and even a place for the authentic creative activity of evil, as long as the kingdom of this world exists. The world here is in some sense stolen from God, who permits this on the pathways of creaturely freedom. But this trial of freedom has its limit; it can and will be experienced to the end. And the end of the trial will come by the power of God, in the parousia, when Satan, despite his solipsistic affirmation, will be expelled from this world, will remain void of being, in the pose of a metaphysical charlatan, no longer deceiving anyone, not even himself. Satan will not stop being a creature of God, for, outside of this, only annihilation would await him. But God does not annihilate His creatures. With hatred and against his will, Satan knows that he is a creature of God, but he does not find joy in this, for he hates God precisely owing to this consciousness of his creatureliness. This consciousness of self is for him the primal source of the burning in hell, of the hatred of God as the source of life, of ontological envy.
But after the expulsion of the prince of this world, Satan’s duel with God begins. (Ibid p.507-508)
Alive but not alive. Alone in the nihility. Nothingness and gloom. Frigidity. Impotence. Inertness and immobility. A bankruptcy of being. Absolute infecundity. Defeat.
In this state, he proposes that the eon long process of demonic redemption begins. "condemned to sustain themselves in an objectless solipsism" (Ibid p.512) And regardless of how strongly they struggle against God... they are inevitably "creatures" and "created beings", unable to hold out against the endless Love of God. Unable to do anything, their delusions will shatter against the reality of their proper truth/understanding: "I'm not God". Which is the beginning of the first step of the long process they will require.
The living out of this contradiction constitutes the only and exhaustive content of the life of the prince of this world in his exile from this world. Can this struggle extend for an infinite (and in this sense “eternal”) duration, a bad infinity, or, having been weakened by the struggle, must he at some point in exhaustion lay down his arms? If his strength inexhaustible for this hopeless and endless struggle with what is self-evident, such that it can fill the ages of ages, or is even such a supposition impossible because . . . Satan, in point of fact, is a creature and only a creature, making his strength and his capabilities limited? What can save him in this situation is precisely that same creaturehood he rejects as a reality outstripping his creaturely freedom. He can grow exhausted in this unequal struggle—rather, he cannot not grow exhausted from it, in the end capitulating before reality and acknowledging that not he himself, but rather God, is his creator, and this means: falling down and worshipping him. Then will there occur an ontological coercion on the part of reality, by force of fact. (Bulgakov, “Apocatastasis,” pp. 78-79)
St Paisios the Athonite once fasted and prayed for two weeks for the eternal salvation of the devil. While praying he saw a dog’s head sticking his tongue out and mocking him. Paisios concluded from this incident that “God is ready to accept the demons provided they repent, but they themselves do not want their salvation.”
This is considered dangerous spiritual territory by the orthodox church, mostly because of things like...
Met. Kallistos Ware tells the story of a four-hour car journey he once had with a Greek archbishop. Hoping to enjoy a long conversation on the topic, he asked the archbishop: “If it is possible that the devil, who must surely be a very lonely and unhappy person, may eventually repent and be saved, why do we never pray for him?” The hierarch peremptorily replied, “Mind your own business.” End of discussion.
The devil's sin is one that occurred before any human sinned. His problems are not ours. His relationship with God is beyond our ability to understand. ... etc.
TLDR//Short answer: St. Isaac the Syrian is a stronger example than Origen.
(for both the catholic and orthodox church perspectives)
