Hello,
According to your description you need a Multi-level user management/access – (super admins, admins, sub admins, teachers, students, parents) these can be students, parents, teachers, management, contractors etc.
I would like to discuss it in broader way as you know Freelancer has words limit and your project is pretty complex.
It would better if we could have a chat on it and discuss about every modules which you have mentioned.
Let me know your thoughts.
Regards,
Martin.