Though it seemed wise at the time Bilbo took the cup, it was actually very unwise, because a dragon can sense when a part of it's treasure is missing, and will not rest until it has killed the thief. This is what made Smaug aware of the dwarves' presence to begin with.
2
He takes it upon himself to save the dwarves, multiple times (from the spiders and the elves most notably.)he was a hobbit who knew how to sneak around places without being seen
Bilbo said, talking to himself, "what have i got in my pocket?" (it was the Ring). Gollum thought it was a riddle and Bilbo decided to make it one. he gave Gollum three chances to guess and gollum lost after four. then gollum went "to get something" (it was the ring), and Bilbo thought he was abandoned and left with the ring on. Gollum thought Bilbo knew the way out and he wanted to follow him, realizing Bilbo had the ring. Bilbo saw Gollum racing towards the gate and followed him to safety.
Gandalf surprised Bilbo and he was foreshadowing the future
Though it seemed wise at the time Bilbo took the cup, it was actually very unwise, because a dragon can sense when a part of it's treasure is missing, and will not rest until it has killed the thief. This is what made Smaug aware of the dwarves' presence to begin with.
The Arkenstone
In the Lord of the Rings, Bilbo Baggins steal the Ring of Sauron, which he made to rule over all the other rings. Bilbo later on than passes the ring on to Frodo Baggins, his youngest nephew, to destroy. This leads to the story, The Fellowship of the Ring.
2
yes most likely
On his first visit to the dragon hoard he decides he needs something to show the dwarves. He grabs a two handled cup and returns with it. When Smaug misses the cup, he makes a ruckus and eats the dwarves ponies.
Biblo 'borrows' the Arkenstone.
No they did not steal it.
There is actually no race in The Hobbit. It was not a race against Time as in The Lord of the Rings. Bilbo's quest was simply to steal for the dwarves, that was it. Nothing is described as a race.
Bilbo trys to steal the troll's wallet. They capture him. The company is also captured. Gandalf comes and turns the trolls into stone.
Bilbo takes the Arkenstone. He isn't entirely sure why he does it, but he picks it up and knew exactly what it was. He had some idea it might be of use later on.
The Stanley Cup is made of sterling silver, thus making the Cup's color silver