I have wondered about this. It occurred to me that maybe it could have had to do with the way Elves percieved reality. Maybe they saw differently. Maybe they always experienced the world as flat - perhaps the reason they could still take the Straight Road even when men couldn't. Perhaps what we have is the Sil accounts of the flat world relating the Elvish peception & the post Numenor accounts being the Mannish perception, & the story of a change in the shape of the world being a mannish 'invention', an attempt to fit their perception with the Elven accounts.
Of course, one would then have to ask why Elrond didn't put Bilbo right! Possibly he felt that as men would be 'running' things from then on, then the Mannish account could be left to stand.
Elvish perceptions have interested me for a while - they don't seem to see the world/reality in the way men do. Legolas sees the 'crown' of flame on Aragorn's head for instance, or his ability to pick out the number of Rohirrim & Frodo's perception of Glorfindel, as a being of shining light is said by Gandalf to be a vision of him as he is on the other side. Which begs the question, do Elves see each other in that way?
I'm sure someone is going to offer lots of quotes to show this is all wrong - as happened when I wrote into Amon Hen (Tolkien Society bulletin), but I still wonder if there is something in it.
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