Hi, Sean.
Yes, you can do this with Show/Hide. Because of using multi-select checkboxes, all of your questions will need to be on the same page.
To easily move all of your questions to the same page, go to Edit Survey => Reorder Questions and drag and drop them. Be sure and save changes.
To set up Show/Hide, go into the question you want to be the trigger question and go to the options that will trigger the question to be shown. Click the green and white icon in the column to the right of the option to set the trigger. A light screen will pop up. Check the question(s) you want to appear once the trigger question is selected. Save changes.
Then go to the question that will be hidden until it is triggered. Go into Advanced Edit (the little notebook on the left side). Go to the Advanced Formatting box and find the Show Hide controls section. Check the box labeled ‘ This question will be hidden unless toggled by a Show/Hide Trigger Question on this survey page’. Save changes.
This completes setting up the Show/Hide for your questions.
I hope this helps, Sean!
–Cheri