I have this kind of entities:
Document | n .. to ..1 | DocumentType | 1 .. to .. n | PropertyType | 1 .. to
I see you are setting the cascade in two places : the @OneToMany and the @Cascade. I think this can be a problem, if one overrides the other ...
The error you are reporting need some more context to be understandable. "Deleting an already deleted entity" involves clearly two operations .... You need to give details about the state before, the operations and the state afterwards (with "state", I mean the state in the database...).