One way I've done in the past for something similar is to model the media library files in a similar fashion as the content tree. Place your files in the correct directory and have a repeater and a datasource get those files based on the path you're currently in.
Another way is to create your own form control which will allow you to link or create multiple files to a page.
Yet another way is to assign add the PDFs as attachments to the document. This does not require you to move them all to the media library but it will require you to attach them all to the page.
Yet another way is to create a linking in say a custom table or a module which allows you to select a page and a media file GUID or URL. Then just repeat through those custom table items to get all the media files for the given URL you're on.