"BUT what will happen to the "history" when we erase these files from our homepages (and if you see rough.jpg, above, you'll see why I want to erase it...)"

The idea is that you shouldn't delete the files from your home page. Otherwise, yes, the image will disappear from the posts that included it.

I guess there are approaches that could be implemented that would guarantee that (future) images are never deleted, but I wonder if it would be too complicated in terms of usability?

Regards,
Craig Steiner
8052.com Webmaster