Proper setup for Observation Checklists

Summary:

Oracle partners. I am seeking to understand the proper configuration for Observation Checklists. When I create one within Self-Paced Learning, I cannot assign Individual observers but, I can add this Self-Paced Learning item to a Specialization. When I create an Observation Checkist within Content Items, then I can add individual observers but, I cannot add this content item to my Specialization.

What I want is:

A Specialization with multiple courses, an Assessment (Quiz) and lastly an Observation Checklist that routes to a select group of Trainers (not Manager or HR Representative).

Issues:

Adding the Observation Checklist (Self-Paced Learning version), then I cannot designate one or more select individuals who will observe and evaluate the Learner.