Yes (with no success though...)
Maybe track matte with several shape layers in a pre-comp will be a bit better solution...
No. Try copying the path, pasting in Illustrator, then align, then past back into AE.
The other option is to use shape layers. You can numerically align them or make each shape a separate layer and align them with the alignment tools.
You could also put each mask on a separate layer, align the layers, then copy and paste the masks back to a single layer.
Yeah, I know of all of those ways. Hoping I could do it all in place. Trying to avoid precomping, track mattes, and copy and pasting.