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Fascinating observation, Sardy, and I envy you the opportunity to read the Hobbit aloud - it's magical when spoken!
This is indeed the stuff of which fan fictions and RPGs are made - I know BW himself once started writing the story of Isengar the Mariner. I have no written evidence to add to the discussion, but would agree that this is one aspect of having a story that began independently and later had to fit into a framework.
As to the girls, it's quite possible that they were mentioned for Priscilla's sake; I have no idea how old she was when they were inserted, or whether they were there from the beginning, when the three sons were Tolkien's main audience. I've always suspected that the mention of the Old Took's three adventurous daughters, including Belladonna, Bilbo's mother, was for her sake. Now where could they have gone on their adventures with Gandalf?
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'Mercy!' cried Gandalf. 'If the giving of information is to be the cure of your inquisitiveness, I shall spend all the rest of my days in answering you. What more do you want to know?' 'The whole history of Middle-earth.. .'
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