Thank you Jochen and Michael for the evaluation and tips! Everyone has been so helpful so far, and I am so appreciative. And yes, William Michael...that's exactly the breakdown of my camera set up. How were you able to assess that?
I ended up getting a friend to model, and feel like I have made progress, though I definitely still have work to do.
I do have to say for the time being I'm probably going to have to continue playing around with speedlights/reflectors, and the softbox I have until I can get a firmer grasp on some concepts and spend a little more money on renting/trying out gear that will help me achieve the look I'd like, or something that at least has a similar pop to it.
That being said, I've attached another image, and would love if anyone has thoughts. Given that I'm working with a much smaller lightsource than Michael identified, I played around and thought this was the best look I could achieve. I've moved my softbox fully center (still w/a parallel reflector to avoie too many shadows), removed the middle diffuser and turned up the output a bit. I (obviously) have a hairlight coming diagonally from behind.
The look is better I think, but I'm curious what others think. I think I may need a third light to separate the backdrop and a softbox over the current hairlight, as it seems harsh. Any thoughts?
PS, Michael Mowery, did you take that shot? From the eyes it looks like the "clamshell" lighting I'm using, but with larger lightsources, and a softbox instead of reflector. Awesome shot!