Interesting point!
I think one thing that makes such a combination relationship possible is if the skater is older. Alissa is an adult. She doesn't need a coach to police her practices and make all her judgments for her. She can now supply a lot of the motivation and a lot of the discernment herself. She needs a coach to analyze her weaknesses and steady her temperament, and maybe give her a push over the hard spots, but she doesn't need a coach to parent her. The same is true of Boitano, who was in his twenties when he competed in Calgary. It may also have been true of Evan and Frank Carroll. The balance of power is less one-sided, though it doesn't take away the coach's duty to point out difficult issues or insist on certain changes of approach. The student is now (presumably) adult enough to handle such things sensibly when they are brought up.
If Caroline is now mature enough for such a relationship, it shouldn't be an impediment that Karen Kwan is someone she knows and likes off the ice. Besides, nothing I've seen of Peter Oppegard leads me to believe that he'd ever be a pushover.
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