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transfer_rotation_to_content (or rather add_transformation/replace_content) do not properly duplicate the contentstream they're modifying. this means that if you pass a pdf-level copy of the same bg_page multiple times, the content will be rotated multiple times but the rotation-property ('/Rotate') will only be changed for the first page
pypdfs docs explicitly say that you should not to add_transformation + merge, but instead use merge_transformed_page, which this now does for everything