I haven't gotten through your whole post yet, but the "postmodernist literature professor" jogged my memory about a trend I've noticed in your post. Postmodernists, and perhaps in particular postmodernist literature professors seem to be a recurring foil. What's going on there? Is a way to break out of that analytically? I sense that as a deeper writer and thinker you'll go beyond cartoonish representations of foils, if nothing more to reflect a deeper understanding of things like postmodernist literature professors as natural phenomena. It seems to me to be more a barrier to knowledge and understanding than an accurate summation of something in our reality (postmodernist literature professors).