This is my opinion about why Damon should win Elena:
Damon is a much più complicating character than Stefan. He is strong, intelligent, always wears a mask to hide his true feelings and in the beginning he is being presented to us as the bad guy who is proved not to be so bad after all. In reality, if we look a bit deeper, we will find out that Damon hides much più behind that mask than we know.
One thing is certain: the main feelings are pain and rejection. While still human, Damon was constantly overshadowed da his little brother, Stefan. He loved his mother very much, yet she had to die...

Mystic Falls is a picturesque town located in the southern area of Virginia. Aside from the towns foundation in 1859 (in the series timeline) da the Founding Families, the town also has a long history of vampires, witches and werewolves. As the Founder's Council, they secretly guard the town mainly from vampires, and they are seemingly unaware of other Supernatural beings, such as licantropi and witches.

The Founder's council:

The Founders Council is an association of the Founding Families, townspeople descended from the original settlers of Mystic Falls, as well as various municipal officials....