The Kingpin and Crazy 88 are both great boats. The Kingpin is renowned as possibly the leakiest boat ever made. The Crazy 88 leaks but not as much as the Kingpin. Going through and Aquasealing every screw in the boat will make a HUGE difference. Some people have said they had issues with their skirt not being able to get a good seal due to cockpit shape but I personally did not notice the issue. While I do not own either boat, I have paddled both a number of times. They are both great playboats for surfing, cartwheeling, aerials, flatwater, etc. (though I liked the 88 better). I also liked the 88 better for river-running (though you may spend some time in the stern-squirt position).