Can I populate the label of a text box with the output of a single item in a multi-checked list?

I'm not sure if this is possible, but my goal is to have a list with a bunch of options, where users can check up to 5 (figured that part out). However, then, ideally on the next page they'd get asked specific questions about each of the items that they checked (the question for each one would be the same, but ideally it would be separate questions).

I can see how to get the total output to populate a text area, but not individual checked items.

I inspected your form and I saw what you are trying to achieve. 

Unfortunately, it is not possible to pass the value of only one specific option that was selected to a label or sub-label of another field. 

You can only pass all selected options. Also, the correct unique name of your checkbox field is {techTrends}. 

As a possible workaround, you can create a separate Text Area field for each of your checkbox field options and then show Text Area fields for selected options with conditional logic. 

How to Show or Hide Fields Base on User's Answer

Here is my demo form: https://form.jotform.com/80882248740967

Feel free to test it and clone it. 

Hope this will help.