Bilbo does appear to have a habit of picking up things that later prove troublesome (the Ring, the Arkenstone). It has always struck me as odd, however, that the Ring -- which is an object of malice and evil with a sort of will of its own -- was something he picked up casually, in the dark, simply because his hand happened to fall on it, and in so doing, it put the Ring in what turned out to be the best place to lead to its eventual destruction. He chose to take the Arkenstone, not just because he happened upon it in the dark, and for him personally, the repercussions were more immediately bad. Just goes to show that Gandalf was right when he said that Bilbo took so little harm from the Ring because he began his ownership of it with pity. Not so the Arkenstone, and in that case, he lost friends in the battle that followed.
I tend to think that Bilbo is very much the embodiment of the Hobbit tendency to be "brave in a pinch." He's really a poet and scholar, and if he yearned for adventure, I think it was mostly because he wanted to know what it was like, to have such an experience so that he could feel he understood the heroes he heard about in story and song. When needed, he displays considerable courage, but doesn't really step up and volunteer for the job very often. I can't help but think that at the Council of Elrond, he volunteered to take the Ring to Mordor with a rather certain knowledge that he would not be allowed to do so because of his age. It doesn't diminish the value of his offer, because he's the kind of person who would stick to his word, but it could well explain why some of the others at the council smiled when he volunteered.
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Call me Ibrin (or Ibri) :)
Originality is the one thing that unoriginal minds cannot feel the use of. John Stewart Mill
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