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After owning an I/O for the last 15 years, I am now just starting to run an OB again. Everyone talks about that outdrive being complicated, and corroding, etc. I just don't see it. Take care of it, change the oil and pump and it'll be just fine. The I/O is also quieter, cheaper to run, smells better,easier/cheaper to fix. The big downside for me is the engine box taking up prime transom cockpit space, so I recommend that you pay attention to the layout and think about that when you look. As far as size, a 23 is a lot more boat - but thats a good thing. And the reasons you want the cuddy are very valid - I struggled with my choice for the same reasons and would have preferred the cuddy if I had my way. I see Seeswirls around, they look nice, haven't heard a lot of negatives, but have no first hand experience.Do a search on the wmi boating board and you may find some specifics.Good luck.
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