I did end up figuring this out and went with 2)
To keep it simple for content creators I told them to make sure the name of the transcript the same name for the pdf. When a new song comes in a playlist, I grab the text from the current track playing, parse the string with WordPress file name URL rewriting (such as ” ” reverts to “-” I believe; this is an older question of mine), tack on “.pdf”, check if it exists, and then if so add an anchor to the PDF below the current title track. Upon click, it opens a modal with the transcript (that was also built with jQuery).
Quite nice as it does also load the the next song’s transcript into the modal if the modal is up and the the current song ends.
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