Okay for anyone doing something similar, here is how to prompt information into a field: https://superuser.com/questions/676110/how-to-prompt-for-information-when-starting-a-new-document-from-microsoft-word-t

Still working on figuring out if one can insert pages based on the field, or some alternative.
Numbering is of course using Ctrl+F9> right click > edit field> AutoNum