I said I was going to post this "tomorrow" about 3 or 4 days ago. Just so you know, this is pretty much my idea of what "tomorrow" means to me.
In other words, there be spoilers
The reason I read books again (and again and again and again) is that I've never read the same book twice: every time I get something else out of it. If I don't think there's anything else I can get out of a book, I won't reread it (unless I'm bored and nothing else is available). What I got out of The Hobbit this time is that pretty much everybody in the book is kind of shitty. The monsters are pure monstrosity: stupid and evil like the trolls, clever and stupid and evil like the goblins, crazy and evil like Gollum, bestial and evil like the Wargs, cunning and evil like Smaug. But the "good guys" aren't so great. Take Gandalf: He's a troublemaker who has no qualms about leading his friends in potentially lethal situations, abandoning them, and hoping they'll work things out on their own. He's a master manipulator who deals in secrets and lies, doling out or withholding information as best suits his purposes (this and many other elements of his character are clearly reflected in the character of Albus Dumbledore). Indeed, the whole quest, we will find out in one of the supplemental works (either the ROTK appendices or the Silmarillion, I can't remember which) is a scheme of Gandalf's to get rid of Smaug: the Dwarves are just convenient stooges (this doesn't count as a spoiler, since it is made pretty clear in the movie). The Dwarves are no better: Stooges or not, they're motivated by vengeance and greed. Even the narrator acknowledges that they "are not heroes, but calculating folks with a great idea of the value of money ..., but are decent enough, if you don't expect too much." Thorin in particular is an arrogant, ostentatious autocrat whose stubbornness consistently puts him and his friends in worse and worse situations.
The rest of the characters have plenty of flaws as well. The Rivendell Elves are certainly the best of them, but they seem flippant and carefree in the midst of a world that is falling apart. The Eagles are fierce predators that would just as soon have picked at the company's burnt bones as saved them, if weren't for a favor owed. Beorn is a violent, misanthropic hermit; the Wood Elves are paranoid, uncharitable, and xenophobic. As for the Laketown Men, you find venal, opportunistic, populists like the Master alongside hardheaded and humorless hero Bard. I'll admit that I'm making a little too much of this, but it seems present enough to be worth mentioning.
Into all of this mess comes Bilbo. Like the rest, Bilbo is a flawed character. At the beginning of the narrative, he is, for better or worse, the perfect picture of an English Country Gentleman: overprivileged, stuffy, and suspicious of anything that might upset the status quo. So it's only fair that his life be turned upside down by the appearance of Gandalf, who apparently considers it an unsuccessful day when he doesn't upset 6 status quos (statuses quo?) before breakfast. Bilbo comes across as whiny and petty early on, but the voyage and the company change him. Like many other journeying protagonists, Bilbo learns that he is a part of a world that is wider and more complex than he realized: there are many good and evil forces at work, and individuals do the best they can in these circumstances for good or for ill. Wicked people make decisions that are meant to be evil but somehow work out for the good. Good people make bad decisions, or good decisions that go bad. Eventually, he stops constantly bemoaning the lack of creature comforts on the trip and starts to see the value in adventuring. This is not to say that he loses his love of easy living, but it is turned into a positive. As Thorin tells Bilbo in his final farewell,
There is more in you of good than you know, child of the kindly West. Some courage and some wisdom, blended in measureIf more of us valued food and cheer and song above hoarded gold, it would be a merrier world. But sad or merry, I must leave it now
I'd like to add that this is the scene in the book that makes me the most misty-eyed. To put it in context, the last time Thorin spoke to Bilbo it was to cast him out of his favor, calling him a "descendant of rats." So it's not just the journey that changes Bilbo: Bilbo changes everyone (well, not the Goblins or the Trolls), softening them, not in the sense of weakening them but making them open to the wonder and beauty of the softer side (okay, that sounds like a Cotton commercial, but just go with it). Even Gollum becomes something less of a monster under Bilbo's influence.
Next time: The Fellowship of the Rings, Book I.