[__MatrixMan__]

I've mapped paired symbols to the same finger on opposite hands, so ()[]{}<>/\'" are mirrored, and then also I've got numbers and symbols corresponding as well so the 123... pad on my right is a !@#... pad on my left. It gets me pretty far, but not everything has a mate so I occasionally have a brain fart moment and suddenly I'm hunting for | even though I have years worth of muscle memory on this layout.

So I guess I'd say: design to lean on familiar structures as much as you can and then just commit to using it a lot and don't give yourself too hard of a time when it gets wierd. Whatever you come up with will surely beat the pain associated with having your right on of pinky in charge of 50% of the symbols plus enter.