I guess it all comes down to the fact that Damon can be summed up with this quote:
As a child Damon was a pure idealist, a gentle soul who was quite caring about those around him and whose quietness was matched by a surprisingly strong courage. Events later in his life led him to become a lot more cynical and wary, but instead of destroying his softer side, he chose to armor it with his pragmatism and more grounded view toward life. Part of Damon’s own journey of self-growth is to find a balance between the idealism he harbors from his childhood and the cynicism that embodies his person now. 
As for the Aeson situation, as far as he’s concerned, the Hero’s probably had to deal with his own problems and is hardly the one at fault for any of the pain Damon experienced on his own or the broken promise that Hades’ made (that fault solely belongs to his Uncle alone). Besides, Damon’s always wanted a little brother.
I would like to try being friends with Hephaestus and Hestia myself; it seems they are the two who may have the more grounded reasons for being against the idea of making the Bearer a Hero/Heroine.
As for the closuring thing, I doubt that the Bearer may get much closure from their past lives; they’ve been reborn so many times,and while the Trojan War was once such moment of their lives, it is hardly the only one they may end up experiencing with Aeson.
Sssoooo…the Bearer may be introduced to their boyfriend/girlfriend’s family during the summer? 
If that were to happen, I wonder how it will go. I mean, we know Aeson’s mom passed away that that he’s an only child, but Calypso has her two little brothers and mother, Adonis has his father and little sister, Avery has her half-brother and her divorced parents , and I’m taking a wild guess and saying that the boy who tries to prevent Sage from jumping the Bearer during the dance may be another brother of hers.
All of my Bearers have this little warning alarm in their head that shouts “STRANGER DANGER; I NEED AN ADULT” whenever she’s around (even Damon, and he’s very flirty by nature). Besides, my Zeus Bearer Pan likes guys and is asexual; he would certainly be the one with even less interest in Aphrodite (funny thing is, Adonis is his intended love interest). 