My ASA 103/104 was on a Beneteau 393, My first charter was a 43 Leopard. I had to get a check out captain the first day since my classes were on a mono and charter a cat. It really helped me get comfortable that first day. The biggest benefit is that he worked with each person on our crew on what they'd need to do when tacking, anchoring, picking up a mooring ball, etc. Then, we went out and practiced picking up balls for an hour, sailed over to Cooper, went over charts. He listened to my trip plan, offered a suggestion or two on things to do I hadn't thought of, then we sailed back and dropped him off. It was money well spent. Instead of just checking me out, he was a teacher for all of us. It was great.