We just built a public app that does exactly what you guys are looking to do:
We were manually uploading photos to merchants stores and building hacky excel macros and decided to just build something. I use the app myself once a week for migrations and customer updates figured I'd share it incase it helps someone else that's looking at the chain here. Happy to answer any questions also!
I assume you are referring to me?
I need to make the tool work for any shopify store.
I should have this done in the next week.
You will be able to auto upload any image to a matching SKU straight from your desktop - Mac Only.
Shopify SKU Image Uploader
If anyone is interested in my Shopify Photo Upload tool, for a short time i am offering it free and looking for beta-testers. It is specifically for matching SKUs/Barcodes with images.
Please read about the product here:
If it is something you are interested in, please contact me via the page.