Thanks for reaching out!
Actually, it is quite difficult to guide you here because it is not clear the user’s case and we don’t know how the db is structured. Anyway, I’ll provide some hints that might be helpful.
If in your DB thing- “Photos” has a type- list of files, then condition- Photos set list won’t work because you are using the Single File uploader. In this case, you can use or Multiuploader instead of Single Uploader or change set to list to add one item.
In case if you have 5 picture Uploader and you’d like to make changes to a thing when, for instance, one picture uploader value has been changed, then when the #1 FileUploader value is changed kick off the workflow and set an action- make changes to a thing and indicate this file uploader value. One file uploader is equal to one workflow, meaning if two file uploaders value would change then you have to set two workflows.
Also, you can find additional info on bubble forum where the community is discussing different user’s cases and much more: https://forum.bubble.io/.
Hopу this was useful!