I'm embarking on a new journey here and looking for any tips from people who've done something like this before.  It's kind of a two-part question
 
I have a service in which two parties are involved. let's call them Shipper & Receiver.  The form used for setting up the service is quite long.  When the Shipper & Received are matched, I need to take information from the service entry, plus information from other form entries (e.g., company logos) and create a document (let's call it "Agreement") that both users can sign online and once both signatures have been added, a PDF is generated and made available to both parties.
 
My thought for Step 1 is to create a new form called "Agreement" and once the match occurs, I create a new entry and copy into it all the necessary information from the other form entries.  Does that sound wise?
Step 2 (question 2), creating the PDF, is eluding me, because of all the "special things" needed to display, such as the company logos and a repeater of dynamic length (i.e., is at least 2 and could be 10 or more items).  I've looked at e2PDF and it seems like I can get part of the way there but not all the way.  If I create a PDF template and assign form fields to it, I don't see how I work the dynamic-length repeater into it such that the fields below it don't get overrun.  If I don't use a template, then I'm just going to get a PDF of the form itself and it's not very pretty.