So I’ve been making some progress and here’s what I’ve come up with based on current feedback.

1. Getting Started:
   1. Tools of the trade: Text Editors or IDEs, resources
   2. Key Concepts: Nodes, Taxonomy, hooks
   3. Base Drupal Install in 20 Minutes
2. Drupal Modules
   1. Core Modules
   2. CCK
   3. Views
   4. Panels
   5. Social Networking Modules (module selection may vary)
      1. Buddylist
      2. Invite
      3. Userpoints
   6. Collaboration Modules
   7. Activism & Advocacy Modules
      1. Petitions
      2. Forward
      3. Event + Signup
   8. Modules for Ecommerce
      1. Ecommerce
      2. Ubercart
      3. When to choose one or the other.
3. Putting it all together (Sample Sites)
   1. Social Networking Site
      1. Modules used
      2. Steps to put it together
      3. Things to watch out for
      4. Suggestions for next steps or customizations
   2. Media Hosting Site
      1. Modules used
      2. Steps to put it together
      3. Suggestions for next steps or customizations
   3. Rating Site
   4. Corporate Site
   5. Small Business Site
   6. Non-Profit Site
   7. Personal Site
   8. Organizational Intranets
   9. Discussion Group Site
   10. Blog Site
4. Making it yours: Theming
   1. Overview of theming
   2. Themeing in Drupal 6
      1. template structure
      2. template overrides
      3. best practices
   3. Examples
5. Making it yours: Customizing Modules
   1. Overview of how modules work with drupal
      1. typical hooks or actions
   2. Determining what you want to do
   3. Find the code
   4. modifying and testing
   5. releasing
   6. contributing back to project
   7. Examples
6. Site Optimization
   1. Performance Tuning
   2. Search Engine Optimization
   3. Module Updates

I think this starts to reflect how people are working with drupal in that people can get started quickly with it; they install it, get a few modules set up, but then they say “What now?” This approach helps them get past that stage and make Drupal fit their own approach to building their sites.