I have a document that has multiple fields for text entry and each of them has a yes/no checkbox next to it. If I need to enter something, I also check 'no'...and then I have to copy/paste what I entered, from all fields, down at the end of the report. What I want is to check 'no' and have whatever text is entered in the corresponding box automatically populate in the report summary box at the end. How do I do this?

You make them as linked Content Controls and duplicate them at the second location.

This page gives a good introduction to CCs Word Content Controls
Both Greg Maxey and Graham Mayor have Content Control addins which help make linked Content Controls easier to implement.

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Andrew Lockton
Chrysalis Design, Melbourne Australia