I have seen questions & posts about this topic since 2017. I'm surprised it hasn't floated up to a development project yet!
For those of us who have thousands of items with at least 1 image per item, we spend countless hours adding in the photos versus working on more important things with our business. It is critical that we provide our customers pics of our products but it take soooo long.
A bulk image upload feature is not a nice-to-have but a must-have!
Thanks!
Square Community