New Drupal User Help: Adding Files Categories to Content Type

Ok I am hoping someone can help.. I am very new to Drupal but trying to learn.

I have created a Content Type that is like a directory of users, the title is the last, first and I have some fields of Last and First for creating some views

the issue I am running into is I want to add groupings of Files to the user but I want the files to have some different type of definitions.

eg. when I upload a file to the content type, I want to specify if this file is an Application Form, Evaluation, Write up and then when viewing a the content, it would list the File name + the File Category + any other definition we would add to the file

Right now when I add a field of type file I can only have it specify a Description..

For Example the Page might look like

Doe, John
application.pdf, Job Application, 6/15/2013
review2016.docx, Performance Review, 2/13/2016
johninsident2016.pdf, Incident Report, 2/15/2016

Anyone can help that would be greatly appreciate..

Drupal version: 


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