Bombadil and Gandalf

[Daisy Brambleburr]

he is a moss gatherer and i have been a stone doomed to rolling."

To me that means that Gandalf is a traveller while Tom stays in one place. Similar to the proverb, 'a rolling stone gathers no moss'.

And as for the talk? I think that Gandalf just wanted to have a chat. Yes, bring out the tea and iced buns!
Maybe your right in some ways about Tom looking after the Shire etc, but I don't really think that he would do that. He seems just to stay around the Old Forest and not to go into the Shire much. Plus, the Shire won't need much care now that the war is over.
I'd guess that Tom was a pretty interesting person (or whatever he is) so Gandalf simply wanted to talk with him. About what? It's a mystery. Or perhaps Gandalf knows more about this 'enigma' than we do. Maybe he knows his real purpose? Who knows?

Boy, that was a mysterious post!