Since most, if not all, answers and comments here are copies of parts the question, or close enough, I shall throw my 2 cents in.
I just want to point out that even if there is a way it is going to be difficult to implement. The logic of it traps us. From a logical stance telling the browser to replace it's cached images for each changed image on a list since a certain date is ideal BUT... When would you take the list down and how would you know if everyone has the latest version who would visit again?
So my 1st "suggestion", as the OP asked for, is this list theory.
How I see doing this is:
A.) Have a list that our dynamic and manual changed image urls can be stored.
B.) Set a dead date where the catch will be reset and the list will be truncated regardless.
C.0) Check list on site entrance vs browser via i frame which could be ran in the background with a shorter cache header set to re-cache them all against the farthest date on the list or something of that nature.
C.1) Using the Iframe or ajax/xhr request I'm thinking you could loop through each image of the list refreshing the page to show a different image and check the cache against it's own modified date. So on this image's onload use serverside to decipher if it is not the last image when it is loaded go to the next image.
C.1a) This would mean that our list may need more information per image and I think the obvious one is the possible need of some server side script to adjust the headers as required by each image to minimize the footstep of re-caching changed site images.
My 2nd "suggestion" would be to notify the user of changes and direct them to clear their cache. (Carefully, remove only images and files when possible or warn them of data removal due to the process)
P.S. This is just an educated ideation. A quick theory. If/when I make it I will post the final. Probably not here because it will require server side scripting. This is at least a suggestion not mentioned in the OP's question that he say's he already tried.