1. I think they represent a guide, a helping hand, and the good side of nature. The guide: They gave advice for navigating through the Old Forest. The helping hand: They provided shelter, food, water, and advice. Tom also helped the hobbits in the face of danger. The good side of nature: Tom is the enemy of Old Man Willow, who represents the bad side of nature.

2. I think it's a sign that Gandalf is coming to Rivendale and that the Road to get there has become harder, with Black Riders searching for them.

3. HE'S A MAGICAL WIZARD WITH MAGIC POWERS SO THE RING RESPONDS DIFFERENTLYYYYYYY

4. The place must have felt calm and peaceful at the time, and the calmness caused them to fall asleep.

5. They called for Tom because they were in trouble. Tom helped them by singing the trouble thingy away.

6. Not sure...

7. I think Mr. Butterbur is a very respectful person who is also a little strict. He is also a pro at recognizing people.

8. Not sure...

9. THE PRANCING PONY, BREE. Midyear's Day, Shire Year, 1418. Dear Frodo, Bad news has reached me here. I must go off at once. You had better leave Bag End soon, and get out of the Shire before the end of July at latest. I will return as soon as I can; and I will follow you, if I find that you are gone. Leave a message for me here, if you pass through Bree. You can trust the landlord (Butterbur). You may meet a friend of mine on the Road: a Man, lean, dark, tall, by some called Strider. He knows our business and will help you. Make for Rivendell. There I hope we may meet again. If I do not come, Elrond will advise you. Yours in haste GANDALF. PS. Do NOT use It again, not far any reason whatever! Do not travel by night! PPS. Make sure that it is the real Strider. There are many strange men on the roads. His true name is Aragorn. All that is gold does not glitter, Not all those who wander are lost; The old that is strong does not wither, Deep roots are not reached by the frost. From the ashes a fire shall be woken, A light from the shadows shall spring; Renewed shall be blade that was broken, The crownless again shall be king. PPPS. I hope Butterbur sends this promptly. A worthy man, but his memory is like a lumber-roam: thing wanted always buried. If he forgets, I shall roast him. Fare Well!

10. I feel like it specifically describes what happens in the future, I've seen the title of the movies, and 'The crownless again shall be king' sounds like the title of the third movie, 'The Return of the King'.