I was a double major, English/Psychology, and I too was obliged to read and understand Chaucerian English as well as Shakespeare. As for Chaucer, "tuning in to that wavelength" is an apt way to put it and that's how I thrived through English 136, the complete works of Chaucer.....I'm afraid that I'd have to re-familiarize myself with it if I ever tried to read his works again.
Shakespearean English is another story, I can still read or hear it and it's as understandable as modern English.
I'm guessing that the English of the future will be evolving and changing faster than it did in the past....everything else in the world is changing pretty fast it seems. I'm 66 years old and the 20-something frame of reference might as well be from a different nationality.