How about a pane for "How to build a static HTML/CSS website" that hides all panes but prerequisites? Then maybe one on how to build a dynamic site (raw, no framework). Then to build an [x-framework] site. Then, the penultimate pane, "How to build a scalable web application with automated infrastructure (prereq: chef or puppet or whatev), advanced monitoring (prereq: Nagios, or whatever that CustomInk/Etsy toolset is called), test-driven development (prereq: Lang-appropriate testing libs), and continuous integration (prereq: Jenkins)"

Definitely agree with you about keeping clutter to a min due to overwhelming. This may be stretch but maybe just another pane appearing on the right third of the screen when you click a box labeled 'Connecting It All' and just providing links to other resources the demonstrate how to connect the technologies highlighted.