Am I correct that once an image has been loaded into a story, there is not a simple way to swap out the actual JPEG while keeping all the metadata, caption, etc. in place? For example, a student loaded an image in one story that is very small, and I’d like to replace it with a larger version of the same image. Is my only option to delete the first one, and replicate by hand the captions, creator, source, etc.?
Yes, unfortunately, you’ll need to delete the existing file and upload a new one, re-adding the file metadata. This is how Omeka works by design, presumably because it is primarily an archival platform, so tying the file to it’s metadata would be a best practice.
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makes sense, even if it’s annoying 
Thanks for the confirmation.