Re: 3; on a side note I also struggle with this perception that Elena should be happy with/flattered by Damon 'being good for her.' Elena is very empathic - compassionate, generous. She takes others' feelings seriously. Callousness in general upsets her, and without Damon taking independent steps of his own towards more genuine readjustment of his worldview, (i.e. acknowledging that hurting other people is wrong, not just 'Elena & Stefan won't like me if I do it) I can't see her accepting that. She's too aware of him as a person that hurts others, their personal interactions aside. And she's too practical to be taken in by the 'romance' of the concept.
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If that made sense?