Say for example, I have 2 singles. Can I have them set to send the coins they mine to 2 different addresses?
You'd have to create two accounts and run two instances of the miner, one on each account.
I'll be adding a "send X coins to Y address" functionality to the website in the future. With that you could manually withdraw 50-50 to two separate addresses. I'm not planning any automatic income split though.