This method is preferable if you need to compose one or more pages of text at the beginning of each section or chapter in your PDF file.  Since this is so you You may as well take advantage of MS Word's navigation feature: Table of Contents.  

In most Word Processors, you can save or export a file in .PDF format.

Here, we'll discuss the simplest method for creating a Navigable PDF file that includes various documents.  There are more complicated methods that potentially provide more and better options, and you can review them by clicking the options below.

MS Word: Write Your Subject Starters

It is important that you have your required files in place and properly arranged in the PDF beforehand, so that you can create your section-starting pages, and their corresponding Table of Contents in the proper order in Word.  Having to move or edit these in Acrobat, after you've added the file there, is more complicated and inefficient.  That said, it is not impossible...

Editing Your Table of Contents in Adobe Acrobat

If you elect to add, remove, or just move sections around, that's simply a matter of using the tools fond in the Organize Pages screen:

Image Removed

But editing the Table of Contents is another matter.  While viewing your Table of Contents, click the "Edit PDF" Icon on the right.

This will create a text box around your Table of Contents list.  You can click inside, and type in the new item, just as you would in Word.  

Then, click "Link" on the upper toolbar.

Adobe highlights the spaces where links work in the Table of Contents.  Now that you added a line (or lines) to the Table, the links going to various pages, below the new additions you typed into the Table of Contents, do not properly light up with their corresponding text.  Rearrage them accordingly by clicking and dragging the link spaces.  

Again, click "Link" on the upper toolbar, and choose "Add/Edit Web or Document Link."  

Click and drag with your mouse, to create a new link space.  Follow the steps in the dialog/pop-up boxes to create the link:

• For Link Type use "Invisible Rectangle."
• Link Action should be "Go to a page view."
• Follow Acrobat's instructions to establish the page to which the new link will go.

As you can see there's a lot of steps and some careful mouse-work to edit the Table of Contents in Adobe.  For this reason, try to assemble everything you need, and build your Table of Contents and Section Pages in MS Word, first.  If you have extensive edits to make to a Portfolio, consider recompiling it a new PDF file.  

When combining files into a PDF file, it's important to remember   Effectively, Word will automatically create the links to various parts of your PDF, instead of you having to manually create them in Acrobat.

If you are importing images as well as text into the PDF via a .docx (MS Word) file, you can perform compression on the images using Word's tool, before bringing the Word file into your PDF.

Remember that Acrobat is not a content creation tool, so much as a document publishing tool.  The distinction is important, because you wish to create the final outline or skeleton of your PDF file in Microsoft Word, and add it to Adobe Acrobat, together with PDF filesafter you have assembled and arranged all the contents of your PDF file or document.  Since editing files in Acrobat is not efficient, you want to avoid having to make changes to the PDF once it's assembledthe skeleton, or table of contents, is developed and added to the PDF.  If you need to subsequently make lots of changes to the contents, organization, and the Table of Contents itself are extensivetable of contents of your PDF document, you may find it's easier just to recompile your files into another PDF, rather than attempt to make changes to the Table of Contents table of contents of your existing PDF, within Acrobat.  

Create a Table of Contents

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.  It's doable, and editable in Acrobat, because it appears that Acrobat converts the .docx internal links to PDF Document Links.  But, two caveats:

• Don't add page numbers in Word.  Once you add the other content in between, they need to be updated anyway.
• if you need to edit the resulting PDF it's a pain, because you would need to shift the links down, and create new ones in the TOC, which is complicated and not for the impatient.  

PDF Portfolio feature in Acrobat

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.  

In short, this is too complicated for most who might read a PDF portfolio, and would result in an untenable support burden for COLI.  

Organize Documents

Now that your documents are installed, 

Rearranging Files

Rotating Pages

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?  

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

Combine the PDF

First, start by compiling all the files or documents you want in the master PDF file or document.  Start by adding these to a folder, or arrangement of folders, on your hard drive.  This makes it quick to add into the PDF, and to copy it all to backup or long-term storage.  You always want to keep these files separate, since you may need to rebuild them into a new, replacement PDF file later. 

Next, combine them into a PDF file, and arrangement the way you want them.  Here's a tutorial.

(Full Screen)

It is vital that you have everything you need in your combined PDF, and arranged in the correct way, since making changes after you've added your skeleton file will be complicated and inefficient.  

MS Word: the Skeleton File

Next, create a "skeleton file" in Microsoft Word (Google Docs or Pages will work, too) that contains the pages that open each of your sections or chapters ("section-starter pages") and a table of contents.  Here's a tutorial showing how to do that:

(Full screen)

Complete the PDF

Add the skeleton file to your PDF file. Move the section-starter pages into their appropriate places within the document.  The links in the MS Word-built table of contents will be converted into Acrobat's method for handling navigation links, and should remain true to your section-starter pages, even when you move them around in the PDF document.  

Here's a tutorial showing how to do that.

(full screen)

It is important that you have your required files in place and properly arranged in the PDF beforehand, so that you can create your section-starting pages, and their corresponding Table of Contents in the proper order in Word.  Having to move or edit these in Acrobat, after you've added the file there, is more complicated and inefficient.  

Page Numbers in the Table of Contents

If you suspect your reader might print out your PDF, you can add page numbers to the Table of Contents.

Editing Your Table of Contents in Adobe Acrobat

As indicated above, it is not ideal to edit your Table of Contents (add or rearrange contents) within your PDF file, since Adobe isn't an efficient content editor.  That said, if you elect to add, remove, or just move sections around, that's a matter of using the tools fond in the Organize Pages screen, and the previous instructions.

Modifying your Table of Contents presents additional complications, however. Here's a tutorial showing how to do that: 

(Full Screen)

As indicated in the video, if you plan to make extensive changes, it may not be worth modifying an existing file.  Instead, you might just compile another, and (re)build the table of contents and section-starting pages in MS Word.

...

Resources

Return the Navigable PDF Guide Main Page

Adobe Acrobat's User Guide and Tutorials: https://helpx.adobe.com/support/acrobat.html

Transcript for the above video tutorials: https://docs.google.com/document/d/1iQRD8_Ih8omkBHYgQG6krhjZV4DfdTJHnssogY7frEM/edit?usp=sharing