Trigger delete DCR/output files and workflow

System

The client doesn't want to train users to execute list modified and submit deleted file(s) after deletion, or to start workflow before deleting the files, or to attach the DCR and potentially other templated output files related to the workflow that is started for deletion. When a user deletes a templated output file it should prompt them to select whether they want to delete the other output files generated from that DCR and the DCR itself, and whether they want to start a workflow for all of the deleted files. I assume this means replace another Interwoven custom menu item (delete) with one that works correctly.

Does anybody have a solution that does anything like this?