>Currently I work at the best job I've ever had, for the best boss I've ever had, but there are some weird things here that frustrate me. ...
>
>My boss is retiring in 1.5 years and the assistant director is much tougher and she will tell people what's what to their face, but she is totally caving with this guy too.

Besides the advice others have given, have you (or anyone) specifically told the boss and assistant director how demoralizing this is to the whole group?