Use Literature & Latte's Scrivener to Batch Update Syllabi
Scrivener is a writing application that is geared toward novelists and screenwriters. It also serves beautifully as a research repository and as a catalog of syllabi and syllabi components.
What do I mean by syllabi components? Each section of the syllabus can be catalogued within template folders in Scrivener's master binder. Within these folders, you can create global elements (name, title, contact information, office hours, class policies, etc.) general elements (rubrics for different courses, supply lists, etc.), and course-specific elements (course descriptions, class times, calendars*, etc.).
Add these elements to new binders to include them by reference and put them in the proper sequence. (It helps to number the elements using a standard naming convention.) You can add the elements to as many binders as you like and they will only point to the original. Changing the original effects the change in all of the binders referencing the original.
When all of the elements in a given binder are selected, the main editor will include all of the elements. Simply print the document to PDF and voila!
*Or, if you (like I) prefer to place your calendar in your course management system, the course calendar itself may be a global item.