Changing the way that inline images are layered and interact with one-another

I gave this a shot, and it doesn't look like the order in which the images are placed in-line affects this layering. For example, if I drag a new image into the document, insert it into the middle of the group of inline images, and then adjust the right-side offset, it still goes under any images to its right.

In my workflow, all of my inline images are placed through a data-merge that inserts filenames, and then a script that finds the filenames and replaces them with the actual images. I could in theory modify the script to insert the images in the order I want them layered, but based on my test it doesn't look like that would result in any change to how they're layered. 

I get that this works for producing the end-result that I described, but I should have mentioned that the reason I'm looking for a styles or scipts solution is that it's on a document with hundreds of these images, which I'm generating on a weekly basis, so I need something that handles this in an automated manner. 

This is what I've got right now. The blue arrow is made up of 4 inline images, the front of which has an object-style that gives it text-wrap and a negative right-side offset, so that the red circle is pulled in overlapping. 

Here's what I want to achieve (easy enough to do with taking the images out of the inline configuration, bringing the arrow to front, grouping, and pasting them back inline, but I need a more automated solution).