Delete Image File on Update page

I have asked this question before, but in a totally different context. And I can't seem to figure out how to do it on an update page.

What I have are 4 possible images for a record. The user might include 1, 2, 3 or 4 images and later update them. That's all fine.

But they want to be able to delete an image and not just update it. So for example a record has 3 image. They want to delete #3 leaving it blank.

What I would like to do is include a checkbox next to each image thumbnail on the Update page. If checked, that image will be deleted and the record table updated when they submit the Update. How would I bind the "File Manipulation" behavior to be triggered by the checkbox if checked?

Thanks,
TroyD