I'm knocking my way through ASP for the first time. I've done several hours of general tutorials, I get the gist for starters and I'm ready to begin working on original ideas. I thought I'd toss this out here since I'm still in a heavy learning curve and potentially save myself hours of chasing bad ideas. I've chosen one of my drawings to start working with, but I have questions about the best way to draw this in the program:

I've read enough discussions to know that part of creating a reliable rig for animating is to draw with the fewest number of points possible. The legs/feet/toes will be pretty straightforward, but I'm wondering about the best way to draw the head. Something as simple as creating the "cut out" hole in the head isn't terribly straightforward. Simple circle, easy, adding the second dimensional curve with the add points tool distorts the original circle. Is this better approached via masking? I'd like to be able to adjust the angle of the cut through as the character moves horizontally.
Same with the open area at the back of the head. I'll have to animate the curvature at the back over horizontal movement. In the area with the concentric curve lines, would this work better animated as points on a layer or translated on its own layer altogether? Given some of the style details in this I thought I'd see if some of you veterans had any advice about how ASP might handle something like this best. It's a hell of a deal trying to break away from adobe mentality! Thanks very much!
Matt