How Do I Dynamically Update a PDF Textbox Using Excel Like Columns Which Automatically Wrap and Size

I am trying to dynamically display a list rooftop units to which are associated to each product our company produces.
Our website is database driven and each product has a link to a PDF file which explains the product, and a "List" of each rooftop unit which this product can be used upon. This "List" of units is changing and are updated constantly. We are currently manually updating each PDF. We have thousands and it has become unmanageable. In some cases this "List" may contain only be several units, in others the "List" will contain hundreds. Additionally, the rooftop units when described are anywhere from 6 to 50 characters long. Therefore, we can't just dedicate a set window to populate the information. The list must flow into the window in columns and be smart enough to best consolidate and wrap itself, so not to use countless pages. We prefer the first page to describe the product and the second page to contain all the associated units in columns with an auto font capability.
We have Acrobat X Pro version 10. We are considering LiveCycle. Everything and everyone says yes it can do this; however, no one can tell us specifically how or show us examples.
I have figured out how to create the "List" in a comma separated string, but it is very confusing and hard to read. Does anyone know how to list the data in a table... in flowing columns similar to an Excel spreadsheet?

I understand why you need updated running headers in your book. To a sighted reader these serve as a guide to where you are and help you find things quickly.  In addition, if you are exporting your data to XML or HTML from the tagged PDF it would also be important to have these in the proper location. 
But for accessibility purposes, it doesn't have to be there because the screen reader reads everything in linear order, line by line.  No one is looking at the page.  A user listening to the screen reader read the page is going to hear this heading, just before the actual word itself. So they will hear the first word on the page twice.  It's not the end of the world if it's there, but such headings are not necessary for accessibility unless they are not repetitive and contain information that is not otherwise available.
So I would say, fine if you need them or want them there, it's just one word. 
I think you should try exporting your book to PDF (or even just a chapter of the book) and look at the tags panel in Acrobat to see if you are getting the result you want.  I can't tell you exactly what you should do to get those results, you are using a plug-in I don't have. 
I can tell you I didn't have to add the headers to any article at all, they just automatically export if the other articles in the file are added and you don't select the header style option "not for export as XML."
You may not experience the same results with your plug-in, but I think it will probably work the same way. 
Give it a try and best of luck.

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