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This is a question that has plagued me ever since my earliest days in web design. Until now, I had not a forum where I could pose it.
Most of us are more than familiar with the concept of font/typeface pairing in graphic/communication design to provide contrast and visual interest. Weather that constitutes two faces from different type classifications (e.g., a serif and a sans-serif or a gothic and a handwritten, etc.) or two or more font variations from one typeface family (e.g., a condensed and a regular width or a heavy and a thin, etc.) is up to the designer.
Generally speaking, we've been taught, advised or simply learned through experience that two fonts/faces provide the best results. Not to say that one cannot use more than two or just one, but one too often we see the schizophrenic or mundane examples of both extremes. Which brings me to my question