“Doesn’t it always come down to the love of a woman?”
For Damon this is exactly what rules him, his love for the women that he loves. Damon had given up being human because he viewed eternal life as a gift because it would give him the chance of having forever with Katherine. Yes, he was aware of what he’d lose, but in the end he chose Katherine, his heart chose Katherine. Eternity in his eyes soon became a curse when he realized that “Katherine” was dead and that’s why he had been so willing to not complete the transition because in his eyes there was no world without her. With Elena he is willing to give up vampirism because he will always choose her in every shape and form, when it comes to who Damon is it’s based on his love of a woman. Think about it when he “lost” Elena, thanks to Katherine he became a mess, and reverted to his old and reckless self. Yes Damon’s love for Elena is strong, passionate, real and all of the above but without her it’s as if his entire world shifts, just as it did with Katherine. His life is based solely on these women and thats why he’s willing to make such sacrifices, because he’s doing it for them, and yes he’ll be happy because he has them, but at the end of the day is that his real choice?
We know that Elena is being ripped away from Damon, we aren’t sure on the how, but it’s happening, and because of this Damon is losing his light, his only light and his love for Elena is what controls him and will make him act out. For TVD S7 if Damon is on a dark and ugly path then the main focus for TVD S7 is Damon analyzing his life and realizing what he wants. With Elena gone he’s not going to have happiness, he’s going to carry her in his heart each second of every day and he’s going to mourn what they could have had. Without Elena there and having to watch everyone else have what they desire Damon will start to long for that. The only thing that will keep him going is allowing himself to dream. Elena had it mapped out on “5 years from now” but Damon didn’t, all he saw was her, because he’s ruled by his love for her, but slowly bit by bit Damon is going to humor himself and allow himself to think about “5 years from now” and eventually he’ll have it mapped out, and that dream that he clings onto, that hope he holds onto because that’s all he has is what will make him want this. Slowly bit by bit his love of being a vampire will fade away, and he will realize maybe forever is no longer enough, because he wants to not just build a life but have a life. There had been a time where more than anything Damon had missed being human, and in TVD S7 that is going to be his journey when he finally starts to let in the idea of being human again. When he finally starts to let that in, and the others around him start to see that he doesn’t want to be human because of his love for Elena, but simply because of his love for himself. Damon has always chosen love, the love of a woman, but this time his choice is going to be based on him, this time he is going to choose himself and what he wants.
At this specific point in time Damon is not ready to let go of being a vampire, because he still doesn’t see himself as human, but in TVD S7 it’s going to be a journey of him rediscovering himself and who he is & I think if done right it could be a really beautiful thing.