[The Saucepan Man]

Well, you have put up a spirited fight, Professor, but I do think that you dismiss the two pieces of "pro-pointy ear" evidence that we have rather lightly.

The first tells us that Tolkien considered the adjectives "pointed" and "elvish" to be equivalent in connection with the description of ear shape. The capital 'E' is not used for "elvish" because he is using it as an adjective to describe a feature rather than a race. This also explains the use of quotation marks. He might similarly have said "hobbitish" in connection with the description of feet when intending to indicate them as hirsute. The point for me, though, is that his conception of the word "elvish" is one that involves pointed ears, so it is likely that he thought of his own Elves in this way, however different they were in other respects form the Elves of popular folklore.

The second shows us that there is clearly a close association between the Quenyan words for leaf and ear. Why would this be if there was not an actual association, most likely a physical resemblance, between the two things, both in the "fictional reality and in Tolkien's mind"? And the association can be made without regard to the speculation in brackets which, in a way, merely confirms the obvious (the relationship). This suggests to me that the "original" Elves (who spoke Quenya) had pointed ears. This may have changed over time, but this seems unlikely - and the quote that you have provided suggests that Elves became less Man-like over time rather than moreso.

As for the lack of any description of Elves' ears other than these references, well Tolkien was not really one for giving physical descriptions of his characters (as opposed to landscapes), in his published works at least, unless this was necessary for the story. The reason for the description of Bilbo Baggins in Letter #27 is because there is very little in the way of a physical description of him in The Hobbit - so much so, in fact, that there was a popular conception around the time that it was published that they were similar in appearance to rabbits! There is, as I recall, scant description of the appearance of Elves in either The Hobbit or LotR. Such that there is relates mainly to their beauty (a general term) and their hair colour (and Tolkien didn't even accord his main Elven character in the latter book, Legolas, that detail).

Tolkien's reference, in Letter #144, to Elves resembling Men in appearance does not, to my mind, in any way preclude pointed ears. I would describe Vulcans as being similar in appearance to Men, although there are obviously features which distinguish them. Moreover, ear shape varies considerably among humans and some can be quite "pointed".

Nevertheless, while I imagine Elves as having pointed ears (and have done since I first read the book), and I believe that the evidence points to Tolkien imagining them in the same way, the lack of any solid evidence in any published "final" story certainly allows ample scope for people to believe otherwise, should they so wish.