I'm 6 seconds into my animation and I like the color and movement I've achieved, but want to add a darker shade to part of the characters to hint at fuller shape and lighting situations.
I managed a simple one-layer shaded mask over the entire animation but to get all the different layers having a correctly animated shaded mask seems way difficult - I was probably a bit naive thinking I could do it in one shading layer.
I know I can copy the full character and offset/distort them and use that for masking instead of a hand drawn shape, but by default this just gives very simple shading, I wouldn't be able to have the shadow dance around from one surface to another as the character turns etc.
Any hints?
I've uploaded a still picture here to give an idea of the flavour of shading I want; the character of course has several layers, bones, etc so its not just nontrivial but too hard to have a simple shape keep up with them

What would be ideal is something thats based on a copy of the character's movement, so basic motion matching is automatic, but lets me easily drag the shapes around from there to adjust it.
I understand masking at a very basic level, I'm guessing this will involve stepping up my understanding of it a few notches?