I got this working and have greatly improved on the functionality. I'd like to submit the changes, but haven't been able to contact anyone. Here are the changes I made.
The plugin, in its current state, uploads the files to CDN, but still keeps the files locally. I have improved this so that the local files are completely removed and every image is stored on the CDN.
The plugin, in its current state, relies on the admin "shutdown" hook to upload files, which breaks it very easily when you're bulk uploading files. I have resolved this issue by uploading the files to CDN and removing them locally as soon as the user uploads the files.
I was able to remove a significant portion of the code (30%+ probably) by addressing the issues above.
If you'd like the updated plugin code that I have created, respond to this in a comment with your email address or contact me via my WordPress profile and I'll send it your way.
This plugin is exactly what I needed.
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