Really interesting your solution is exactly how I was taught Shakespeare and Beowulf in 10th grade. We read beofulf in the bilingual version, and then read Grendel, a modern retelling (which was hella trippy). We read Hamlet with all the commentary to understand the early English, and then had assignments to "translate" it to modern usage. We watched the Romeo + Juliet with the guns. We watched 10 things I hate about you.

For me there was something valuable about working to understand this person from across the gulf of centuries, and realize that what he was writing about wasn't so different than what we experienced. Hamlet's ambivalence. Romeo's horniness. John Donne's sexy mindfucks... What were we talking about again ?