Interesting write-up Keb!
You left out one family member for Regina–Xavier! Cora got love is weakness from Xavier, Henry Sr. Father. I’m not the only one to wonder if Henry. Sr actually is Regina’s uncle or father :P. Xavier was a ruthless King. He didn’t respect his own son even if he did not abandon him, and he talked Cora into marrying Henry. Sr. even knowing she had an imp lover! What a piece of work that guy was.
I think some of Regina’s DNA obviously has that ruthlessness in it, so it isn’t just from Cora’s side. I also found it interesting how Cora and Rumple had parallel father problems. Their fathers were irresponsible and drunk, but of course Cora’s never left her until she left them. Regina’s parents never left her either, until she pushed them out of her life. Xavier on the other hand tried to basically make a puppet of Henry. sr., and a little bit, that is what Regina almost did with Henry.
“If I had a world of my own, everything would be nonsense. Nothing would be what it is, because everything would be what it isn't. And contrary wise, what is, it wouldn't be. And what it wouldn't be, it would. You see?” -- Lewis Carroll, Alice's Adventures in Wonderland & Through the Looking-Glass