It "was good" that Bilbo lost his matches because the flicker of light and odor of sulphur (that a match would have produced) could have attracted potential dangers in the darkness, like Orcs or other creatures. Tolkien plainly states this in the same paragraph.
Because if he had had his matches, he would have been able to light a pipe, and that would have attracted much unwanted attention in the dark. And it might have allowed the goblins to find him as well. The light and the smell of the tobacco would have brought them out of their hiding places.
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Bilbo put a letter on the spoons to Angelica so they were for her
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.
Bilbo by nature is good hearted, sacrificing and loyal, he would give up his life for the betterment of others and this is what made him a true hero.
Bilbo's escape plan is mediocre. He risked the lives of the dwarves while trying to carry it out.
Bilbo never intended to keep the Arkenstone. He only took it because he saw the feverish greed that overtook the Dwarves when the saw their long lost treasure. Knowing how badly Thorin coveted the Arkenstone, Bilbo kept it and later used it to bargain for his share of the treasure (which he intended to share with Bard and Thranduil). What it revealed was that deep at heart, Bilbo was a good person and only wanted to do what was right. It was why Gandalf was drawn to him in the first place.