Example Use Case:
Can multiple merged documents be sent in 1 email?  And if so, would there be 1 document (comprised of several merged documents) with multiple places to sign (1 for each document) using A5 Signature app? Or if that is not possible, can one email contain several documents with an eSign link for each?

App Expert Reply: 
There are different options to achieving this but requires some configuration and not a feature available out of the box. The solution would depend if you want to send documents for eSign sure or just PDFs. We would suggest that you combine your documents into one template and send one for signature. You can use conditional merge sections to include things or not if needed in the one template and page breaks.

Or you can create a process to generate multiple google docs and save the google doc url to fields on the record. Then maybe automate creating eSign doc records then creating some VisualForce email template to send one email with all related eSign links.
Our app premium support team can assist you in configuring a solution as a service and discuss process improvement for why  separate documents are sent and signed.