In this:
class Administrator(models.Model):
user = models.OneToOneField(User, primary_key=True)
account = models.ForeignKey(Account)
class Meta:
It would be
unique_together = (('account', 'user__username'),)
if I understand what you're trying to do. Note the double underscore. That's how you look at a foreign key's object's properties.
What you are missing is abstract = True
in the base class. This creates a table with all the fields for the subclass.
I don't believe you can do what you're trying to do using django core. As pointed out in this answer to a related question unique_together is enforced at the DB layer. If you inspect the DB tables created by django model inheritance, you'll see this isn't possible for the DB to accomplish.
Take a look at that related question for some alternative solutions.