Actually… I came up with a really easy fix that works if you have a second domain available and can match the directory.
Okay, so for anyone Google searching this down the line, this is for you.
First, I made a complete backup of the website’s database and a zip backup of everything.
I created a separate zip backup of the “/images” directory and uploaded it to a vacant domain that I have in the same position. I renamed the “/images” directory on the current site to “/images-old“
Then I used the Plugin, Broken Links, to detect & modify those newly broken links. Within “Broken Links”, there’s an option to search for links that meet the criteria you enter. I searched “domain.com/images” as my term. It displayed the few hundred images that were going to be replaced.
I went to the top right-hand corner of that plugin, selected “Screen Options” and changed the maximum displayed posts to fit all the links that showed up with the search. Under “Bulk Options” I selected Edit. I entered “domain.com/images” as the term and “otherdomain.com/images” to replace it.
After this was done, I verified that the images were loading on those pages from the “otherdomain.com” page. I tried running this plugin here, but it kept hanging on me, plus it kept processing over the pages that didn’t need anything completed, so I ran the plugin “Import External Images“. The only minor issue I had was due to the fact that the old Drupal site I imported from years ago still had remaining image glitches, such as missing thumbnails. When I ran “Image Teleporter“, it would import the empty images. When I ran “Import External Images“, it would kindly tell me there were dead links.
I hope someone found this post useful. I have been looking for a solution to import the images into WordPress for a long time.