Solved! If anyone is ever looking for something similar.
1) Put all the information that needs to be filled out on one document.
2) Create a pop up and fields using this method : https://superuser.com/questions/676110/how-to-prompt-for-information-when-starting-a-new-document-from-microsoft-word-t
Mine looks something like this { SET myfield { FILLIN "my prompt text" } } { REF myfield }

3) Instead insert pages automatically use the "IF" function pasting the full text of the needed page in the last set of quotation marks, mine looked like this:
{ If {TRIM "myfield"}="Manhole" "MANHOLE DATA SHEET ..."}
4) At the end of all your pages use Numbering by : Ctrl+F9> right click > edit field> AutoNum