Characters like Tim Drake and (superboy) Conner have a problem because their whole identity was built around being the “new kid”. So when a new generation comes around they are left with very little direction and purpose. Batman and Superman and other adult superheroes are to popular ( and lucrative) to ever fully leave the stage permanently. And every new generation of writer wants to leave their mark by adding new characters to the mythos. Thus you wind up with a crush in the middle. A bunch of characters that aren’t the new kids anymore but will never be the head liners. It’s the major flaw in DC’s legacy idea.