Full 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)? Or if that is not possible, can one email contain several documents with an eSign link for each?

Consulting Reply: 
There are some options to achieving this. But requires some configuration. Nothing strait out of the box. Do 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. I’m not sure what your use case is why you need separate documents sent and signed. 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. It is possible to create this process just need to develop it. We can help create it if you want at $175 per hour as a consulting service, please submit free case to support to put you in touch with consulting team.