+1 for this
Here’s the typical issue (and thus reason it’s something we want to do)...
We allow content editors (often not web savvy) to create channel entries, and sometimes these channel entries will include a link to a file (which they can upload for themselves).
When the channel entry is deleted, it would be nice to remove the uploaded file also (in order to prevent orphaned files).
However, all this makes the assumption that the file:
a) Isn’t going to be used again
b) Isn’t used by another entry
To take care of a) and b) might require more work - either asking the user if they’d like to delete any associated files (when the entry is deleted) and possibly keeping a ‘reference’ count against the file - so that it can only be deleted when it is no longer referenced by any channel entry.