Hi @Cormac_Kerrigan For #1 for such things when there’s not a UI option like “columns” they are not admin configurable.
If the info IS there in the html then userstyles/extensions can hypothetically be used, otherwise userscripts/browser-extensions to use the api to surface that data.
#2 Is there a X…
There is no bulk-editor, or CSV behavior for the files admin or specifically for file images.
Be sure to file a feature request directly with shopify support, or PLUS MSM if applicable about this migration pain.
It’s either A) for some small set of files use the theme system, or B) for lots of files the api be it with scripts, custom apps, or third party apps/services.
If you A) are familiar with shopify theme liquid and B) already know all the file names and can get them into a CSV list then make a liquid layout/template that spits out the files/urls formatted as a CSV string.
Using the filename and the file_url filter , or file_img_url filter if you want to try and crop/resize images 
Keep in mind the shopify files admin may modify file names in some situations such as for uniqueness.
Roughly and untested:
{% liquid
# UNTESTED filenames may need be to be broken up into multiple runs to stay within theme/memeory limits.
assign filenames = "filename1, filename2,..." | split
for file in filenames
echo file | file_url
unless forloop.last
echo ','
endunless
endfor
%}
For apps/services based ETL process of images for products, etc
- a dedicated image importing app https://www.google.com/search?q=shopify+bulk+import+images+app
- “spreadsheet”/data apps like matrixify, highview ez-exporter.
- apps with integrations for excel ,google-sheets or airtable etc etc etc
- services such as make.com or zapier etc etc etc with integrations for excel, google-sheets or airtable etc etc etc
- Or an automation app like mechanic to script custom ETL behavior. https://tasks.mechanic.dev/?q=file%20
There is also the free shopify-flow automation app that has a google-sheets row integration but you would need to use the advanced send-admin-api-request action and figure out the scheduling/looping for LOTS of files.
?For the deep divers doing platform migrations there was https://github.com/Shopify/shopify_transporter
If you need this type of automation built custom then contact me for services.
Contact info in forum signature.
ALWAYS please provide context, examples: store url, theme name, post url(s) , or any further detail in ALL correspondence.