Attach Specific Document Types in email template
Because you are able to define each document type which is uploaded, I WOULD THINK that you can make an email template that attaches all documents labeled as user defined "Document Type" to an EMAIL TEMPLATE. IF you can add this feature it would make the process 100x easier.
ie If job status is set to follow up - send email template "follow up" Attach all documents with type as "follow-up documents"