Currently we have the ability to send reports through Print Management, automatically during Purchase Order / Sales Order Confirmation. Today, we can have only single report being sent as PDF, HTML, etc.

This does not cater to the business scenario, where along with PO/SO confirmation, users would like to send multiple documents like, Assembly Instructions, Measurements and Designs, Special Handling requests. 

If we can have a "Purpose" field (just like for contacts we have) with options of "Attach in PO / SO confirmation email" in the document handling and Print Management handles this while sending the emails for different purposes. 

This feature can be extended for Invoicing, Picking List.