Please excuse my illiteracy, but your world views and literature are a heck of a lot reader-friendlier than Chaucer’s stuff. I appreciate your efforts!
I suspect, if I were trying to communicate to his audience, Old Jeff would have to act as my interpreter.
I also think he was a very bright fellow. Using characters traveling in a pilgrimage, to tell stories to entertain each other, was an excellent way to weave a tapestry of tales into a longer work.
I have a scenario where people are traveling together for years on a star ship, and even with his example it didn't occur to me to do that!
We've gotten so used to the notion that travel is a boring waste of time that it doesn't occur to us to have passengers entertain each other, and yet the only really interesting thing going on, other than potential calamities, is the life story that each individual carries into that situation.