How to change the text of the “You are about to permanently delete these items…” alert message when deleting media from the media library?

You could use the gettext filter. See the examples here https://codex.wordpress.org/Plugin_API/Filter_Reference/gettext. In your filter you will add code to check

  1. IF it’s the exact text you want to change
  2. then if the users meta value is what you are looking for

the return the revised text.

Else return the passed text unchanged.

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