Design - Ideas on using Pages, Learning Plans, Courses, and Folders to best organize and support Learning

I am curious how others organize their learning material to best support learning.

Here is my scenario: 

1. Large amount of learning resources (videos, slides, PDF, quizzes and certification exam)
2. Multiple audiences with different requirements (NEW vs Experienced but new to company vs. Returning)

My objectives are to organize the training to:

1. best utilizes adult learning theory to support actual learning and adoption
   1. keep it structured and well organized
   2. Not have a list so long that it becomes intimidating or discouraging at any given point
2. make it audience specific 
   1. A New inspector with no experience and needing everything gets what they need in the order they need it
   2. An EXPERIENCED inspector only gets what they need, without all of the foundational material
   3. A RETURNING inspector who previously completed the training only gets UPDATE material (what has changed in the past year?)

I think I could use the following but would like others experience and ideas so I don’t create something unnecessarily difficult to maintain!

1. CUSTOM Landing pages based on Groups that presents the Learning Plans they must complete in the ORDER to complete them.
   1. Once they have completed their Learning Plans they would be moved to the Inspector group that has just the general landing page with announcements, references, new courses, updates, continued training, etc. 
2. Is there a way to make a pre-requisite for a Learning Plan?  I looked, and didn’t see one, but I may have overlooked it.
3. Organize Learning Plans organized by Courses which are organized using folders so that there is not any list longer than 20? items
   1. How many items is too many?  Too intimidating to complete? 
      1. I don’t think it is strictly based on TIME, because a learner doesn’t know how long it will take them, they would just see a long list. 
      2. It is finding that balance where the list isn’t too long and intimidating, but the items are small enough to provide a sense of accomplishment and encouragement.
4. What is the balance between the complexity of the design (and therefore MAINTENANCE and ADMINISTRATION headaches) and benefits to the learners?

I will share some of my ideas, please share yours.

Background: I come from a higher education environment and often still think in line of College > Department > Major > Courses in organization, but I now work for a business and have had to shift to Branch > Group > Learning Plan > Course.  I know, they’re parallel, but I think there is more freedom for creative structure/organization in business. I want to be able to think outside the box.