I usually DO cast into the wind and here is my thinking:
1. The fish are typically facing into the wind. By casting into the wind the lure is coming at the fish from the front and it can see the lure coming a longer distance away. By casting with the wind, the lure approaches the fish from behind which seems un-natural.
2. When casting with the wind, as soon as the lure hits the water the boat is drifting TOWARD the lure. So during the retrieve you have to crank the reel much FASTER just to get the lure to move with its normal action through the water. So if you're trying to burn in those DC10s in moderate to strong wind they really aren't moving through the water all that fast.
But on the other side of the coin, by casting into the wind from a boat drifting with the wind you are casting into water that the boat has drifted over already, potentially spooking fish. ( and of course you have potential for more backlashes too but with some practice and proper setting of the brake, things work well)

Ty, have you seen a difference in success in your boat with experienced fishermen based on casting into or against significant wind?? Thanks!
C.S.