I\'m building an application that allows for large amounts of photo uploads at once, and wanted to know what the best setup would be to tackle this.
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I'd never seen Cloudinary before your mention, but it seems like it'd be a great fit for your project.
First and foremost, it could potentially greatly simplify your app. Cloudinary supports direct uploads from the browser via its HTTP API, and there's already a jquery plugin for it which is based on jQuery File Upload and has similar features, including client side pre-upload processing.
Furthermore, it supports on-the-fly transformations similar to dragonfly (also a very nice lib).
This means that, unless you really need to upload those images through your app, you can completely circumvent it, uploading straight to Cloudify and handling image cropping and other transformations through their transformation API.
You could eliminate Carrierwave and S3 from your app if desired, and there'd of course be no need for any background dynos to handle image processing. Additionally it'd likely be much faster (direct upload and on-the-fly manipulation vs uploading to your app, processing, then uploading to the cloud), and would eliminate the bandwidth for uploading through your app.
Even without direct upload, it seems that Cloudinary provides a Carrierwave plugin which could still make use of their transformation API, obviating the need for your app to process images.