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Lloyd, To answer your question, you need to fully understand about the various parameters affecting depth of field. Please do go through course “How to get blurred out of focus background” where I clearly explain all these.
To achieve your objective, it depends on what focal length lens you are using, how far you are from the subject and finally the aperture. Depending on these parameters you can calculate if you will get enough DoF to get multiple subjects in focus.
Rgds,
Sudhir