Couldn't you use the same painted shader, and have the population using 'invert density shader'? You'd just need to erase the parts you wanted and invert that.
*EDIT: If the paint shader is bigger than the population bounding box, you just need to erase each part in each area that the new populations will be, I think you could do it with one painted shader.
Or, if you really do need multiple painted shaders, create a large enough object(sphere with 'visible to camera' unchecked) with its bounding box lined up along the edge of the previous painted shader's border. You could use a disc object for curved edges. Line the disc up over the first paint shader and use the 'inner radius' size until you are seeing the border, switch to the new painted shader and if you paint on the disc while it's just above the ground you'd get a nice clean edge to the paint while the outer radius will be the mask, then just delete/disable the marker objects...