I suppose if I had to try and defend the theory, I would be more likely to try and posit that the Bombadil we see with the Hobbits, may not at all be the Bombadil that Aragorn or Gandalf or Gildor may know.
Perhaps he was secretly having a laugh on the Hobbits and their rustic non-sense rhymes and dittie's like the 'Man in the Moon'. But his ring-a-ding-dillo's do really seem to be the order of the day, as hinted by Gandalf saying what an unsafe gardian he would be for the ring.
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The dwindling Men of the West would often sit up late into the night exchanging lore & wisdom such as they still possessed that they should not fall back into the mean estate of those who never knew or indeed rebelled against the Light.
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