Why was this group shot more difficult to make than individual portraits?

First the technical: I was shooting a single speedlight in a medium softbox with a black foamcore background. With a single person you can stick that softbox right next to their face off to one side and you have this gorgeous directional light with nice beautiful falloff into the shadows. From there you can work with the pose and tweak the light to get the portrait that works for that person. I brought just one light because I’m still learning about off camera flash and really want to explore the possibilities of using just one light. With two or more people, things start to get more complicated. If your one light is off to one side, the light will hit a group of people unevenly. The person closer to the light will be more lit than the person farther away. There are multiple solutions to this of course. If you move the light farther away, the people become more evenly lit but the light becomes harder. If you swing that light closer to in front of them, the people become more evenly lit but you lose your directional light and the shot looks flatter. You can also have the person who is farther away take just a step closer toward the camera to try to even out the distance. I chose a combination of these three things.