I've not seen a response from others, so I'll chime in. If the answers are not in sufficient detail, I can find someone else to go to the next level.
Requirement 1: The key thing to keep in mind is that PDF Generator is a server-based framework around word, at least for the word to PDF part of its functionality.
1-1) Conversion of Word to PDF... PDF Generator does this well. Note that it will require the installation of MS Office or will use Open Office. Given your fidelity requirement, you probably want to use Office.
1-2) The integration of dynamic data is less clear. PDFG does not support this directly, as we use MS Office. I'm not a Word expert, but if you can pull of the dynamic content access and have the appropriate access paths available from Office as it is deployed on the server.
31-3) Both Output and PDF Generator use a common service called Assembler for the merge. This should be an easy usecase.
Requirement 2: Generation of PDF from a template.
The best product for you is LiveCycle Output. It will take a template from LiveCycle designer, either static of dynamic, and create PDF at moderate volumes. I'd suggest that you look at Designer, including its template import facilities, and then consider how you can get the data for your placeholders into XML format. Output is then quite easy to do the data merge, formatting, and PDF generation.
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