I like Cobalts very much, they are gorgeous and well-made, and I can say from experience that the R5 is a pleasure to operate, but I can't imagine a Cobalt bowrider would make a good Rattlesnake Island boat. I think a simple boat with fat rub rails, an outboard engine, and a self-bailing cockpit would be better suiting for island use where weather could trap you in a bowrider and a cold snap could cause freeze damage to your engine late in the season.
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