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Change highlighting approach
Right now I have 1 div with a MASSIVE translucent border-radius (as the overlay).
A much better approach would be to use 1 simple element as a full-page translucent overlay, then create a second element that serves as the highlight box (pretty much just a transparent box with box-shadow, lower z-index than target). The target element is then set to pos:rel (if necessary) and it's z-index is boosted to a higher-than-overlay value.