Groundhog Day reformed Bill Murray, so I suppose it can reform Lana Parilla. Rumplestiltskin was reformed by Belle. Of course, the whole curse thing was carried out by him even after he was reformed. Rumplestiltskin always succeeds in his long term plans but being a reformed character, the rewards of success can only confirm him in his goodness. I must say that the show is amazingly positive about Rumple.
Re Henry and Regina, Regina is the kind of mother who'll make him go to bed at night, and go to school, and eat his vegetables, and wash behind his ears, and nag him about getting into a good college. He is always going to prefer Emma and the youngest grandparents on the planet.