[egypturnash]

> I can draw people relatively well, but they never look like the people I'm actually portraying. And my drawings are very 2-dimensional, which is a conscious style choice that nonetheless doesn't lend itself well to real-life portraits.

Look at some masters of caricature and cartooning, find photos of some of their favorite subjects, think about how these drawings exaggerate what's there in the shapes of the subject's face/body/motion. This is how you make a drawing that is simultaneously a stylized 2D rendering and one that "looks like" its subject.

Like, get some coffee table books of Hirschfeld or Sorel or someone else who did a lot of caricatures of celebrities and study the heck out of them. Copy some of their drawings with photos of the subjects close to hand. Look at a person and ask yourself what they'd do here, and draw that.

Hopefully this is something your teacher has already gotten you doing! But if they haven't, then give it a try, and see what they have to say about your attempts.