If I had the chance to speak with Bilbo at this point in the book, I would have plenty to tell him. I would first tell him that I think that he is very brave. Next, I would tell him that I have some advice for him and to listen closely. I would attest to the proposal that he should spy on Smaug to attempt to locate his weakness. I would say that he needs to take advantage of any opportunity to take out Smaug as soon as it presents itself.
I might suggest that they try to trick Smaug into thinking that they were somewhere far away from the mountain and steal his treasure while he is away. In my opinion, they should try to avoid to much direct conflict with Smaug. Despite the fact that there are 14 people in Thorin and Company, Smaug is extremely powerful. Smaug is capable of causing many casualties, and that is something that should be avoided if at all possible. Finally, I would tell Bilbo that he needs to continue to be brave and selfless and that I wish him good luck.
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