Welcome back,
Aaron!
I'm afraid I have to disagree with you about Smaug. He invaded two countries, killed or drove away their inhabitants, and destroyed or took most of their property. I certainly don't feel sorry for him; because he didn't express any sorrow or remorse for his actions, yet alone attempt to compensate the relevant people, or at least their descendants.
Even if we ignore that, his response at finding out that Bilbo and the dwarves were assisted by the Lake-men was to attack and begin to destroy the town. Not only was it a vast overreaction; it also led to his death.
If he had just flown around, set fire to a few empty but visible places, and sent a threatening message that any future assistance to his enemies, such as dwarves, would be an 'unfriendly act', that strategy might have worked.
There is the seperate question of whether Smaug or any other dragon had the free will to chose good or evil, which is an interesting one. My own answer is 'Not enough information to give a definite answer'. We don't see any dragon in Tolkien's works
discussing such a possibility of free will with anyone or even with themselves, and if they themselves were free to make such a choice.
I remember a newspaper cartoon which I've been trying to locate, which had a dragon at a podium addressing a seated group of knights, saying that though they had their differences, the fact that they could be in the same place together without using violence was a step in the right direction.
