Looking closer, the Hunter 23.5 has two versions, keel and centerboard. The OP does not say which one he has, but I imagine the keel. Both it and the Catalina 250 have transom-mounted rudders. To me, this makes the outboard more of a problem if also transom mounted b/c you have to "set it" to power straight forward while helming with the tiller which you also have to keep it from hitting the prop of the outboard. Maybe there are some true pros here, but I always found it a real PITA to keep the OB and the tiller/rudder working together in lumpy conditions, requiring both hands at times. So, if you're out there in your 23.5 footer and need to power dead into a strong east wind at from 2 to 5(?) n.mi. out, lumpy-bumpy conditions all around--then

-- how do you think it might go?