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Was just reading this thread and i was in a similar situation this summer. I learned on a sunfish and a 14' Tanzer. This summer I went in on a 23' O'day with a friend. It was a slight adjustment, but the basics are the same. I had been looking for a 19' O'day, great day boat/trailerable and also accomodating for a night on the hook. I wouldn't go any smaller than the Mariner though, especially if you want the option of a night on the water. 19' to 23' I think would be good for you.
Good luck!
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