I have taken several runs at searching the forum and reading the Prince documentation in order to find out how to generate a PDF with an outline (where a left window column appears in the PDF viewer to allow for hierarchical document navigation). Could you point me to documentation or sample HTML/CSS in order to accomplish this.

Thank you.

The bookmark-label, bookmark-level, bookmark-state, and bookmark-target properties are used for this. The default HTML style sheet makes the heading elements h1-h6 generate a hierarchical bookmark tree.