Quite interesting questions and speculations. I quite agree that Tolkien had in mind the idea of 'unlikely hero' who is older, less handsome, less what you'd overall expect in a hero, but who ultimately fares as a hero. As far as I know, this 'life begins at 50' theme was unique to him.
In the context of middle earth , Bilbo's late adventure was prompted by a series of events: Gandalf's meeting with Thorin being the one that started all. From Bilbo's pov, one can say he was rescued from a life of laziness and mediocrity that overpowered the Took sense of adventure that still lay hidden in him. Frodo's adventure though was delayed by Saruman's misleading of Gandalf concerning the Ring's whereabouts. If Saruman was not a traitor, Gandalf would have acted on the spot and Frodo would have began his journey much sooner than 50.
Imladris - what do you mean when you say:
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They were both drastically changed when they were 50: Bilbo for the better and Frodo for the worst.
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