I think most folks handle it via a custom field(s). At least- that’s what I do. It depends on whether I have a variable number of files/images/whatever how I handle it- and whether I also want to display them independently. Sometimes I’ll set up a separate weblog- entry each file/image as an entry- and then have a relationship field or two where I can relate those files back to ‘main entries’. I can then show them with the main entries using reverse relationships. Or- I’ll just plop them in a custom field in the ‘main’ entry if I need something simple.
I know Mark has an extension that allows you to do a simplified file upload associated with a custom field- and it will also handle multiple files in that field.
But that said- I don’t know of anything exactly like what you’re talking about.