[DiapDealer]

There's no way to delete any kind of file (image or otherwise) that will result in all links to those files being automatically removed. The links have to be deleted manually, or with some sort of regex cleanup. Once all links are gone from the html files, the Delete Unused Media tool will show all images that are unused and can be deleted.

It's definitely something that a plugin could be created to do though. Have the plugin present a list of images to delete, and then parse all the xhtml and remove any img tags that refer to the deleted images.