"Choose new file" in bulk

Is there a way to intelligently replace the source files for a large number of related items in a project?

Specifically, I'm talking about the drum stems (EZ-drummer). I realized towards the end of a mix that one snare was slightly out-of place, so I went back to re-render the whole kit. Now I have 26 files that I want to replace with the updated files without manually doing them one at a time

I tried selecting all the media items > F2 > Choose New File... but that replaced all the media items with the same new wav

Then I tried selecting only one of them and toggling on "Update all similar items in project with new filename" from the same menu, it only updated the one I had selected.

This seems like a really obvious feature that Reaper would have, much like how if you rename a folder in your sample library, it can find all of the missing samples on load after you find the first one, but I can't seem to piece it together.