The last point, about Ancient Greek read in the "modern" pronunciation (with Φ, Χ, Θ read as fricatives rather than aspirated stops) reminds me of how Mandarin, which is how Chinese poetry is often read nowadays, is not great for representing the sounds of the poetry as written, since it's lost all final stops (-k, -t, -p) in closed syllables. Other topolects such as Cantonese preserved them, which makes it a better…
Plays of Shakespeare is similar much of the rhymes and inside jokes are lost now due to modern pronunciation of old words. http://originalpronunciation.com/GBR/Home
Some take this to be a bawdy anatomical pun, expressing the young man's hopes of 'standing' in his lady's 'grass' — a distinction lost nowadays that the pronunciation of "grace" and "grass" have grown so far apart.
(Line 88 of Chaucer's General Prologue, https://chaucer.fas.harvard.edu/pages/general-prologue-0)