A century ago, Nobel literature laureate Rudyard Kipling, advanced the proposition that six critical lines of inquiry were fundamental to knowledge: What, Why, When, How, Where, and Who (Kipling, 1902) Had Kipling been writing today, likely he might have added two more honest serving men: Which and Whether. Knowledge derives from learning. In common with any significant, high-stakes, important undertaking, knowledge of real estate investment – its theory and practice — is a central critical success factor. Learning is the intended byproduct of education. In the 21st century that education is expected to be both rigorous and relevant, concurrently sound in theory and practical in application. Real estate investment knowledge — specifically, how real estate investment theory and practice are conveyed through education — can appropriately be considered through addressing Rudyard Kipling’s Six Honest Serving Men – Plus Two.