Ok for my work we handle a lot of calculation documents. All of these have coversheets and revlogs that must be generated. We can easily create an excel file that has most of the information needed to fill in the forms but automating the actual process of filling in these forms that are premade in word has proven tricky. I used macros to some success but if something about a specific form differed to greatly the entire thing would mess up and I still had to open each word file individually and then hit the macro. 
Some of this process isn't going to be automatable as it requires pulling information from pdfs that isn't always in a standard format but any fast automation would be better than none. I have a good bit of c++ experience (by a good bit I just mean several courses on data structures etc, nothing way too high level). I have also used python some and stumbled my way through visual basic a tad.
Any idea on how to go about automating generating sometimes 100+ of these forms?
MS-Word has extensive programming capabilities built in ("Visual Basic for Applications (VBA)" These exact same programming capabilities are available to applications you write in any language, including C++, that can access Word via COM. Depending on your needs, it could be possible to fill in an entire Word document from one click to run such a program.
What would be the best way to automate filling in a premade form in word