Gandalf knew hobbits are made of stern stuff, he also found it amusing to send Frodo along on this adventure I think, and he had this feeling that Frodo would be great burgler. Call it instinct.
As he says he is the only wizard who goes itno hobbit-lore...
You can study them for years, and yet they can surprise you in a pinch! (or something like that)
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My body is broken. I go to my fathers. And even in their mighty company I shall not now be ashamed. I felled the black serpent. A grim morn, and a glad day, and a golden sunset!
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