Question Trouble with 2D sprite Skinning Editor Auto-generate Weight

I'm using the separated png method to skin and animate a 2D character. Whenever I try to generate the weight for my skeleton it only applies weight for the bone highest in the parent hierarchy to the all of the geometry. However, when I only use one bone per island of the sprite it separates the weight accordingly for some reason. It also worked once out of about 25 attempts after deleting and recreating the skeleton several times. When I try to hand paint the weight the program lags to the point where its almost non-responsive. Its worth noting that the PNG I am using is pretty massive at 4096 x 4096 pixels. I am using the most recent stable version of Unity.
^ The problem I am having

^ For some reason this skeleton kind of works?