Intriguing question. I always though the reason Tolkien may have chose that is the idea of an 'unlikely hero.' Of all people in Middle-Earth why a widening girth grocer type of a hobbit? Why didn't Gandalf a more younger hobbit? Because of wisdom. I think most younger people would freeze up when it came to situation they were unfamiliar with. Would a younger type of hobbit even try to attempt something so simple as the guessing game with Gollum?
The impertience of youth probably would have killed Gollum, as Frodo suggested in the Fellowship. Now if Bilbo had not pitied Gollum, where would we be in Middle-Earth?
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"If I knew all of the answers, I'd run for God."
~ Klinger: M*A*S*H
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