Actually, I don't have much experience with a cutter rig. A friend of mine and dock neighbor owned a Newport 30, which we were racing for God knows what reason - this boat was a tub of cement - but he decided to add the cutter rig which would augment his 150, so as to get more speed. I didn't know anything about the rig and he knew a bit more so off we went in the purchase of the sail and the installation process.
The day we picked to test the rig was blowing about 15 to 18 knots and it was just the two of us - the blind leading the blind. Long Beach, Ca harbor has 3 or 4 oil islands - most visitor think they are condos because they are disguised to look that way. Anyway, I'ive never sailed that fast on his boat. We had an awful time keeping the boat under control and fequently had to duck behind the oil island to figure out what to do next from a sail trim stand point. We never did figure out how to balance all the sails on that boat and never did use it in a race. He told me he used it once in a single handed race - yeah, right!!