[Mugwump]

One of the first things I noticed about the Prologue is it contains frequent references to and information about events that occur after the events of the rest of the novel. Apparently Tolkien is happy that readers will know in advance that many of the central characters who will be going into all sorts of dangerous situations during the course of the War of the Ring will survive. Interesting and unusual for a Prologue, but I think it's effective and does not detract from the rest of the book. As Fordim Hedgethistle explains above, one of the purposes of this Prologue is to treat the fiction of the book as being historical and derived from older primary works, rather than a fictional story told by an author.

The next thing I noticed was a questionable grammatical usage, and I'm unsure, because I know that Tolkien was a master the language, whether it's just a typographical error introduced during the publication, or was done on purpose. I was taught that "farther" and "farthest" should be used (instead of "further" and "furthest") when discussing purely physical, geographical distances. Yet we read on page 7 about the three Elf-towers on Tower Hills, that the "tallest was furthest away, standing alone upon a green mound."

Originally Posted by Fordim Hedgethistle

This is one of those wonderfully simple sentences that Tolkien so often writes that open up into all kinds of complexities when you pay it a bit of closer attention. How, in the name of Eru, can Hobbits keep the “laws of free will” because they are “The Rules”? This would appear to be a contradiction in terms: “free will” would appear to mean freedom, and a lack of constraint – the ability to do as one chooses; but “The Rules” (capitalised no less) would appear to be the precise opposite – one follows rules and does what they say. ... I don’t think that this really is a contradiction, but it is a very complicated kind of statement, and one that goes to the very nature of the story that is about to be told.

I think there is a much less complicated explanation for this. The text is that the Hobbits usually "kept the laws of free will because they were The Rules (as they said), both ancient and just." I believe this is simply a matter of an idiomatic difference between British English of Tolkien's time and the English of today. Simply, laws in the text refers to the laws of the ancient kingdom. Tolkien is not saying they are the "laws of free will"; he is saying that, regarding the ancient laws of the King, the Hobbits kept them of free will, or in modern idiomatic American English, kept them of their own free will. Note that free will is not capitalized, as one would expect if Tolkien were making of it a title, "the Laws of Free Will." In other words, of free will does not modify laws but modifies the verb kept. Therefore, there is no contradiction. Tolkien is merely saying that Hobbits kept the old laws of the king not because they were legal rules, but chose to keep them because they believed they were proper and just rules to live by.