I've bee following this thread and had a thought, The most fun ride - OR group ride - I can recall was the scavenger hunt ride of, well many years ago. The idea was that we were in small groups, 5-10 bikes. The goal was not the ride itself but the destination. It was goofy enough to be fun with only occasional mach retard opportunities. It also had group conferences just to find a destination with riders switching off who was leading based on who knew where we were going or what we were going for. Perhaps a change in the focus of what a ride _is_ might help. IDK just a thought.
Not this: