Customized Items Requiring Proof Approval

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I've searched high and low for a solution but I'm guessing what I've been hired to do is a bit out of the ordinary.

The company I'm interning at is selling a product that requires an image from the customer. The image will be sent to a vendor, a proof created and then approved by the customer before the product ships. The sale has already ended this is just a post-sale approval process.

The company runs its site on Wordpress if that's any help.

Here's a very rough workflow of what I am trying to do. Even if you can advise on how to automate a portion of this that would be much better than the current email bonanza going on with the proofing process.