Pat this is a known issue. The File component does not react to changes in its underlying model. You may have to find the component in a snippet and refresh it manually.
Here’s a workaround using a template component. Skuid__c is the reference field to the skuid__Image__c object.
Thanks for posting the workaround. I really appreciate your willingness to post the answers to your own issues - when you find them. It makes this community much richer.