There's a chapter in the Unfinished Tales called "The Quest for Erebor" that explains just about everything that Gandalf was thinking and how much trouble Gandalf had in getting Thorin to take Bilbo along.
Basically Gandalf wanted to get rid of Smaug and reestablish the Kingdom Under the Mountain so that it would act as a stronghold to guard the North.
And, yes Thorin was the one to approach Gandalf about help on their quest.
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...finding a path that cannot be found, walking a road that cannot be seen, climbing a ladder that was never placed, or reading a paragraph that has no...
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