I think this discussion about the direction for Nightwing mention some good points:
The Batman office is a "safe" place for Dick, since he won't be send to the limbo (even if he is mistreated). However, Dick can't grow in the Batman office, because he will be only a "sidekick" for Batman.
However, even if Dick left Batman office, DC won't allow Dick to be part of the Justice League (since they don't want Batman to grow old), so he can't grow outside of Batman office either. Dick might even be at risk leaving Batman office.
I don't think this will change when the higher ups retire, because the new higher ups will still want to protect Batman from old age.
The only time Dick was allowed to grow was outside of Batman office as Nightwing in New Teen Titans. However, this grow was allowed due to the extremely popularity of Teen Titans at that time.
So, Dick will probably need an extremely popular and profitable new direction to be allowed to grow.