I have recently returned from my business trip to Wisconsin for ten days, and it seems I have missed a lot. I will have to read this third chapter before I get more in depth, but here are some of my thoughts as well.
Tolkien definately makes a connection between Frodo and Bilbo, and also a difference. The connection being Frodo and Bilbo both got "adventurous" approaching their 50th birthday, and the fact that they also have the same birth date. Frodo through the beginning chapters also goes on a lot of advice from Bilbo (which I believe has been specifically pointed out). There is a quick distinction between Frodo and Bilbo I caught with a deeper reading. Bilbo is the only person to willingly give up the ring (with some help from Gandalf). Bilbo had carried this ring for what, some 60 years and he gave up the ring fairly easily. Frodo has the ring for a lesser 17 years, as far as we know barely ever uses it (if he even does) and is already reluctant on "destroying" it. Instead of throwing it into the fire like he wants to, he puts it in his pocket. I'm sure 17 years of this ring would already have a hold on people but seems like Bilbo was able to last out longer then Frodo, and resist longer then Frodo.
Aiwendil posted
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Gandalf is the archetypal wise, dependable mentor; his presence tends to impart a sense of security - he may not be infallible, we realize, but as long as he's there, we know that our heroes will have the best chance of success.
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This is quite true, with an example right of the top of my head, it was stated in the Siege of Gondor, whenever Gandalf was around the hearts of men rose, but when he left they sunk again. Gandalf is definately a mentor, leader, and one of the more powerful people in Middle-Earth. Thing is if Gandalf isn't there leading the men or people they quickly sink back to their old low morale. As I read one I will probably find out examples but this is one off the top of my head.
and...
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the reader must at this point try to imagine what sort of thing might prevent even Gandalf from showing up when he says he will.
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Not only that, but also what events happen when Gandalf, or atleast a mentor (for example Aragorn) aren't around. You have the troubles with old man willow, the black riders, and the barrow wright (which if it wasn't for Bombadil who knows what could have happened). This is an early stage of the hobbits where they aren't used to the world out there and they have a lot of growing up to do.
You finish the book with Gandalf not going to the shire, telling the hobbits they must do this alone, and they succeed, because through their journey they have grown, to the point where they don't need someone like a Gandalf around (although it's always good to have a Gandalf around).