If we raise to 50c and CO has a solid diamond then he has to call 40c into ~$1.10 to see one street to hit a diamond?

Not sure why you're saying that anything apart from leading flop is awful then discussed whether you should call or raise in your last post for about half the Skype conversation

I over-simplified my explanation as to raising for information, I should have said maximizing your EV over the hand. We don't gain enough information by raising to make it worth the loss vs the optimal option.

Looking over it all, I agree that leading is the best option, but I don't think think there's that much difference between calling and raising as a 2nd option.