I've watched snippets of the current episode, particularly the DE scenes, and I just want to point out that Damon didn't say he liked vampire Elena better. He has stated it once, that he'll l’amour her either way, and I believe him. Yes, Elena wouldn't be Elena without her humanity. But people forget that being a vampire amplifies that, along with everything else. And I think that's what Damon loves about vampire Elena, her becoming so much plus because she feels more, she lives more.

A lot of people misunderstood the scene where Elena was getting Damon to admit he liked her better that way. In a way, there's a truth in it. He likes this Elena who can now see the world in shades of grey. Before, she can only look at it in black and white. She can only live a certain way because her vues are limited and there are those with expectations from her. But now, in my opinion, she understands the world better, both from the tragedies of her life and the experience of being a vampire. And also, she doesn't care what other people think so she experiences more. She'll eventually turn the switch back on, she'll be Elena with her humanity again, but with a whole new perspective.

And I'll also admit that Damon likes her this way because he's less scared of what she thought of him, considering she doesn't give a damn about anything right now. But that doesn't mean he would rather have this Elena forever. People are dumb and blind if they don't see the effort Damon does in order for her not to lose herself. He restrained her from killing. If Damon wasn't planning on helping Elena turn it back on, ou care about her humanity in the first place, he would've let her kill the woman on the road. He even looked upset when Stefan told him she fed on someone at school. And he's the taking the responsibility to take care of her. Stefan and Caroline both turn to him for directions. That's because he's the only one who can take this version of her and still l’amour her unconditionally.

So I believe that this little road trip to New York is a part of Damon's plan. I was confused, and curious, as to why he retrieved a photo of him and another guy. But I have a feeling that this is he's way of making Elena realize that there's still hope. Her entire family is gone, but he'll get her to see that maybe not all is lost. A poster (I'm not sure is real) a dit that her humanity is the only thing she hadn't lost, featuring her and Damon. If it is real, I think its a good indication of how this storyline will turn out: Damon will bring back Elena.