Your project description really caught my attention. I'm extremely interested in your project because of it's related to woocommerce. I am very confident to fullfill your requirement asap. I'm an expert in making new plugins for woocommerce, I've great experience more than 10 years in this field.
Which template and when to trigger and whom? customer or admin?
Waiting for reply,
Jaypalkumar,
(wc expert)