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Why does Gandalf think Bilbo would make a good "Burglar"? Gandalf 'felt' that he was bolder than the other hobbits and he decided to have Bilbo join Thorin and his company. Gandalf never explicitly said why he had chosen poor Bilbo to join him and the dwarves in their expedition, though. What is the first problem Bilbo and the dwarves encounter on their quest? How is the problem solved? I suppose that the first problem Bilbo and the dwarves come across is when they need...