This guide will help you assemble a PDF format portfolio for various career purposes, such as job-seeking, promotion, and tenure. You may not need or use every tutorial here, but they should generally show you what's possible and can help you with specific parts of the project.
PDF Files: the Basics
Scanning paper documents into PDF
Scanning
Creating a searchable (and possibly editable PDF) from a scan
Creating PDF Files or Pages using Microsoft Word
https://www.youtube.com/embed/-yUS89t3Alg
Is it possible to enact this plan? Create a skeletal document using Microsoft Word, that includes a clickable TOC. The TOC only highlights pages where the faculty member will provide some sort of introductory page. So when you assemble the final portfolio, you put the scanned or otherwise collected documents in among these introductory pages, such that the clickable TOC is entirely built in Word, rather than having to fuss with it in Adobe.
Combining PDF Files
Combining files into a single PDF file
What file types will Adobe include in a .pdf?
Adding files to an existing PDF File.
PDF Portfolio
In this mode Acrobat creates a PDF container that includes files in their original format. Thus, a .pptx file is still editable (and probably extractable) as .pptx. When viewed in Acrobat Reader, these files are still in their original format. This could cause complications for less patient readers, since A-Reader does not automatically preview these files. Adobe purports to include web pages, but in my test it handled https://www.canisius.edu/academics/office-academic-affairs/academic-institutes-and-centers/center-online-learning-innovation poorly.
Adding Page Numbers to a PDF
Is it possible to have Acrobat create the page numbers, and then after that, add the TOC? So that you get the entire document exactly the way you want it, and then as a last step add the TOC?