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

Combining PDF Files 

Adding Page Numbers to a PDF

Creating a Table of Contents for a PDF Document

Create the Table of Contents using Microsoft Word

Creating a Clickable Table of Contents using Adobe Acrobat

Resources

https://helpx.adobe.com/support/acrobat.html