"The closes I've come is rigging a figure right to left then rotating it's base 90 degrees along the y axis. This is okay, but not ideal if  front to back symmetry was just available."

Looks like you are correct here in rigging and rotating to get the proper result with symmetry front to back. I just tested my example and can see the problem. That's what I get for questioning the practice of an artist that's probably rigged a thousand tentacles, ropes, chains, and tubes ;)

Thanks for teaching me a new trick Davo :)