Idea for a workaround worth testing: When a file is uploaded, update the page with a hidden field (using a file.create:after hook) and use this field value to determine if the other field should be shown. Don’t know if this works without refreshing the page, though.
You would have to update the field value when files are deleted.
Thanks, I will look into this. If this requires refreshing the page it would be not usable for me.
I might open a feature request for this on GitHub, as I think it might make sense to give the when property some extra power (also it would be useful to allow triggering when a certain field does not have a certain value).