This troper and his Junior-year English class in high school had to deal with SirGawainAndTheGreenKnight as well as TheCanterburyTales. He and his mates got the hang of it, though he was never confident of his own ability to decipher it (the modern English translation was always available in-book). Come college when he had to read Canterbury Tales again--but only in the original middle English, albeit with
helpful footnotes--he found that though the spelling was somewhat counter-intuitive in comparison to modern English, they often were close enough to modern English to be decipherable (again, with a little help), and the pronunciation, though strange, follows the spelling more closely than modern English; some of his college classmates did have trouble reading it, however. Long story short, YMMV. He did play the trope straight through occasionally mimicking Shakespearean speech in conversation and in poems.