I've already added the mod so that uploaded files are associated with the username. It's a great mode that makes searching for files to delete a little faster.
The utlimate, though, would be for the deletion to occur automatically.
I am using the application as an internal design approval system. The turnover rate on the uploaded designs is quite high, so I would like for images/files associated with a deleted post to be automatically deleted.
I guess I will just have to upgrade my hard drive over time 
Thank you -boRg-