Seek recommendation, idea or solution for creating training manuals

[gimme_this_gimme_that]

We have a department that specializes in training our field staff.

Employees of the department (our customer) maintain approximately 200
training manuals.

Right now, for each manual they maintain separate documents:

1. The student guide (called the participant guide), AND
2. The instructor guide (called the facilitator guide)

The facilitator guide includes all the content of the participant
guide - but also announcements and question answers
which appear on separate pages and in the margins.

The page numbers of the facilitator guide and the participant guide
are in sync.

So the page numbers for the facilitator guide might be
1,2,2,3,3,4,4,4,5,5, ... etc.

The customer wants a solution where the table of contents is auto-
generated and where the table of contents of the two manuals are the
same.

So both the facilitator and participant guides must have the same page
numbers on the table of contents.

The customer is familiar with Word and uses PCs - but they are open to
a slick out of the box solutions.

A solution where the participant guide is created by running a Word
VBA macro when editing the facilitator manual would be ideal.

Any recommendations, ideas, or solutions?

Thanks.