In the scene this section's title comes from, Aragorn makes judging "As he ever has judged" sound pretty easy, doesn't he? Maybe it was simpler for him because he already knew in which direction his path lay. But there were times when even he wasn't sure what decision to make, or second-guessed himself afterward. The Lord of the Rings is driven by people making choices. Is there any way to judge whether they made the right ones?
That's a loaded question. Can we ever judge whether anyone else is right or wrong, morally or spiritually speaking? When asked what Gollum's fate was after death, Tolkien said that was beyond his scope. It may seem extreme for him to decline to judge even a fictional character whom he, after all, created, but it's really not surprising. Not any more surprising than the fact that Tolkien created a cosmos that seems to have no hell for mortals. The Void is created for Morgoth and his demonic followers; its purpose doesn't seem to be for punishment but rather to keep them from causing even more harm to creation than they already have, so sending a mortal there after death would be beside the point. A possible exception to this is Gandalf's command to the Witch-king at the gates of Minas Tirith: 'Go back to the abyss prepared for you!' In Following Gandalf, Matthew Dickerson commenting on this passage says that the Witch-king "...has long since ceased to be of human kind but is of the spirit realm." I'm not sure I agree with this. In his basic nature, the Witch-king is a Man. He is a Man, though, who could still cause a great deal of harm, which makes him different from most human beings after death.
Is it surprising that I don't find it surprising that a Catholic would fail to supply his subcreation with an obvious hell for mortals (just because one isn't mentioned in the Red Book or Translations from the Elvish doesn't necessarily mean one doesn't exist)? Don't Catholics believe in hell? Yes, orthodox Catholic teaching includes a belief in the existence of hell. But in one of those areas where orthodoxy is silent, there's no article of faith that says we must believe that anyone's there. Not any humans, at least. Tolkien's Void is a parallel to hell in that it was specifically created for angelic beings.
The existence of hell is necessary for free will to have its ultimate choice for or against God. If the choice didn't really matter, free will would be a charade. Catholic teaching isn't about to go that route.
But something else Catholic teaching isn't about to do - something it's avoided for 2000 years - is to judge that any individual human has ever made the ultimate choice against God. Only God has enough knowledge and understanding of each person to make that judgment. When the Church canonizes a saint, she's saying "We're sure this person is in heaven," and there are so many canonized saints they have to share feastdays. But in two millennia, perhaps beginning with Peter's statement that Judas went "the way he was destined to go," the Church has never presumed to officially say of anyone, "We're sure this person is in hell."
There have been Catholic practices that have been misinterpreted as saying that, and I think that misinterpretation is a major reason they were done away with (thank God), such as not burying people who committed suicide in consecrated ground, which wasn't an infallable statement about the person's salvation (or lack thereof), but a way of avoiding any appearance of condoning the practice. I've seen excommunication equated with proclaiming damnation, but even those condemned as heretics in past centuries were believed to be capable of being saved (the "merciful" reason for burning someone at the stake instead of, say, beheading: it gave them time to repent). I think the Church has become more trusting over time of the ability of people to make the distinction for themselves between seeing an act as objectively wrong and passing final judgment on the person who performs it. Hopefully we're up to the task.
In the debate of Finrod and Andreth, not published until after Tolkien's death*, there's a line that sends chills down my spine. During this discussion between an Elf and a human about the ultimate fates of their two peoples at death and at the end of time, one of the characters makes the statement that Ilúvatar will not allow anything to ultimately separate His children from Him - "not even ourselves" (emphasis mine). In one way, this could be seen as incompatible with orthodox Catholic belief, in which our free will makes eternal separation from God a possibility. We need to take into account that it was one of the characters who said this, and Tolkien was often quick to point out that just because a character - even a good and wise character - said something didn't mean that he agreed with it, and these two pre-Christian characters have a limited understanding of God's will by the very fact that they're pre-Christian.
But even within orthodox Catholicism, the statement might be seen as a possibility, since we have no knowledge of whether anyone ultimately makes that completely free choice for eternal separation from God. The statement is one "pole" of a paradox that Catholic belief is careful to hang onto both ends of. If the Hound of Heaven** never stops pursuing us, if the One will not allow anything - not even ourselves - to separate us from Him, what part does our free will play? After all, in both our primary creation and Tolkien's secondary creation, the One has been so careful to safeguard our free will that rather than take it away from us He allows us to sin. This is one of those paradoxes that may always put us in the position of the small child who doesn't see how it could possibly be cold on a sunny day.
*Writing the debate seems to have been an effort by Tolkien to make sure that in his subcreation there was nothing that would be incompatible with the Truth of the Incarnation and the Christian beliefs surrounding death, by having representatives of the two peoples who are Children of Ilúvatar discuss these things with each other. (Regarding the Incarnation, this is also the place where we find the belief that at some time the One Himself will enter into creation.) Individual characters, of course, didn't have to hold Christian beliefs, but in order for Tolkien's cosmos to be identifiable with our own, the overall plan of it needed to be compatible with the Truth of our primary creation. For the best discussion of this piece that I've found, see the related chapter, "Point of View: Whose Myth Is It?", in Verlyn Flieger's Interrupted Music.
**This is an allusion I dropped in "unconsciously at first ," only later realizing that it's possible not everyone is familiar with it. It's from a poem by Francis Thompson (a poet Tolkien admired, BTW), speaking as someone who has spent his life running from God - Who never gives up pursuing him.