"It seemed unfair that anyone should possess (apparently) perpetual youth as well as (reputedly) inexhaustible wealth."
Rather than trying to do a coherent post for each chapter, I'm just going to jot down some thoughts that particularly strike me on this reread. I've read LOTR in excess of a dozen times at this point, and each time I read it, there are new things that seem interesting or important.
I'm struck by Bilbo's separation from the rest of the hobbits. Because they are so insular, they are really unable to understand someone who has had an experience that they have not shared - even when that experience happened more than half a century earlier. They look at him with enormous suspicion in spite of the fact that 110 out of his 111 years have been spent in the Shire.
I love how Tolkien just launches right into the story as well (once we get past the prologue) with Bilbo giving away the ring and leaving the Shire.
"‘But I felt so queer. And yet it would be a relief in a way not to be bothered with it any more. It has been so growing on my mind lately. Sometimes I have felt it was like an eye looking at me. And I am always wanting to put it on and disappear, don’t you know; or wondering if it is safe, and pulling it out to make sure. I tried locking it up, but I found I couldn’t rest without it in my pocket. I don’t know why. And I don’t seem able to make up my mind.’
‘Then trust mine,’ said Gandalf. ‘It is quite made up. Go away and leave it behind. Stop possessing it. Give it to Frodo, and I will look after him.’"
This puts us smack into the middle of the story. The last 60 some years is the beginning, which we skip entirely.
Hobbits are so remarkably resistant to the pull of the ring. Bilbo's changes from being in possession of it for so many years are really minimal under the circumstances (he feels thin, "like butter scraped over too much bread," a lovely, hobbitlike description). A man would have joined the shadow, and an elf would have been completely corrupted. Even Gandalf recognizes the danger that would come from being given the ring by Bilbo.
And yet Bilbo is able to freely and voluntarily give the ring away, which has, to my knowledge, never happened before in the history of the one ring.