Updating a list with a data set within a dataset

I have a Learning management system that I am trying to build.
When I updated the Lesson with a new document for review, I want to send an email and update a datalist to show that the user now has a lesson to complete.
A user might be in more than one group and there may be more than one group in a lesson.
I want to only add the unique values to the data set. And if the training existed before I want to reset it or the new line will just include a version or date of the training.
If I built this backwards let me know.
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