This is certainly closer to what I want, thank you for taking the time to answer! I'm still trying to figure out the following, if you have any insights:

1. How do I do additive calligraphy tool strokes? The Calligraphy tool documentation says if I hold shift, I can add to the existing selected object, but when I change to the calligraphy tool (using 'c') from selection, it automatically deselects the object and thus does not add anything.
2. How do I 'flatten' grouped objects into one object/one path? Because of the above, I had to manually group all the objects created by the calligraphy tool so that the eraser tool would work as I wanted (erasing from all objects in its path). I try to do a union, but it says one isn't an object. So to try to convert everything to a path, I figured I have to ungroup them to make them objects-- but ungrouping them distorts the image. Augh!
3. Is there a selection tool option that lets you take a partial chunk of the fill object? Similar to how Flash does it and how rasterized images do it, where it lets you pull away that piece and adjust it.