Simplify Proofing Process - Seeking ideas

I'm trying to figure out a more efficient way to do proofs for my customer. My current process is copy the artwork, dump it in a PDF template, send the PDF, do revisions on the original, dump it again in the PDF....... etc. It's tedious and prone to errors. 

In a perfect situation, I'd like to create the art in Illustrator, and click a button and it creates the proof for me. I'm not familiar with writing scripts for adobe, but wouldbe willing to hire someone to set this up for me. But perhaps there is already soemthing that I haven't discovered yet?