How to automatically assign a training every year

Summary:

We have the following scenario:

Learners are required to complete some mandatory trainings every year and they should complete the training within 90 days of it being assigned. But if the training is assigned to learners after October then they should complete it before 31-dec of that year. So the system should:

1. Assign a course to learners with a due date of within 90 days of their start date
2. If the training is assigned after october 1st then the due date should be 31-Dec of that year
3. The course should be assigned every year regardless of whether an employee completed it or not. And the system should maintain a record of previous years complete/incomplete status