If a Leave Keeper is submitting leave for an employee, and is submitting as “automatically approve” with prior supervisor approval, will the supervisor still need to go into HIP to approve?

No.  If you select the option to “automatically approve” a leave request entered on the Create and Maintain Absence Requests screen, the HIP system will automatically approve the request and it will not trigger an email notification to the employee’s supervisor, nor require the supervisor’s further action.