That would be fun issue. Cass goes to a game show and ends up winning a trip to Hawaii for the entire family. Bruce, Dick and Barbara are working together in a Riddler case, but they decide that the kids should have fun. So you have Tim, Steph, Cass, Jason, Harper, Luke, Jean Paul-Valley, Michael and resurrected Damian in a small plane. Harper has been trying to get water out of her ears, so she starts jumping and she trips over and falls into the cabin, making the plane crash. Tim and Steph confess their love and Jean Paul confesses that he cheated.
Batman learns the news and says:
They would probably look at each other and say "I didn't know having repeated sidekicks was so important to Batman. Was that guy so great?"