Provided those filling the form can use macros, and they have Word 2010 or later (as Word 2007 and earlier do not have check box content controls), then what you ask is relatively straightforward using the exit event of content controls to evaluate the results entered and check the appropriate check boxes.
For more information and background, my old friend Greg Maxey has a useful tutorial at
http://gregmaxey.com/word_tip_pages/...om_events.html and
http://gregmaxey.com/word_tip_pages/...l_entries.html
His site has lots of valuable information about the use of content controls.
Yesterday, in another forum thread, I posted the attached document which demonstrates an unrelated use of the Exit event to produce calculated values, which can be used to see how the Event works in practice, before you dig in and alter your form.