Struggling with Files and PDF Thumbnails in Drupal 7

I'm working on building a document library in Drupal 7. The project has presented a lot more challenges than I initially anticipated, and one of them is the presentation of files. Each entry can either be an internal only entry, or be visible to the world. Each entry can also contain multiple files, and each of those can either be internal only or visible to the world. I am migrating from another system with a lot of content in place. In the current system, each entry has an optional cover image, files are just listed by filename. That's where the trouble begins.

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