I have ran into this issue several times now – where I grade an exercise and offer some constructive criticism , and then the person who has submitted , in this case @ryanocerous777 asks a few questions. However , frustratingly , I can see no way to help out further or continue the conversation….. are am I missing something?

It would be great if this worked more like the forum where you could continue to reply and offer help rather than be limited to just one comment.
As for your answer @ryanocerous777 – I am no pro lighting expert but it is all about trickery and faking things to get the effect you want. So yes , I would agree with using a plane or some sort of light mask to limit where the lighting hits the face. You could even get clever with playing with transparency on the mask object to let a percentage of light through. I have also used textures with transparency to get some pretty cool lighting effects.
For Aaron Paul , a spotlight may work if you played with the “size” and “Blend” settings to blend it out nicely so it is not a perfect circle , but also think about the material that you are casting the light onto – in the ref , his head almost looks a bit glossy , as if he was sweating – so you may have to do the same for your model in order to get the correct effect. Hope this helps 🙂