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I second the "get a smaller boat" theory. If you are going to stay inshore, stick with a single outboard walkaround 23-25 ft. Seaswirl, proline, hydras, wellcraft, robalo, century, cobia, etc... there are millions, and you can't go wrong as long as you have a survey and pay the right price. This is the time to buy too.
No boat is cheap and without small problems, so don't expect it to be reliable like a honda. And don't let anyone talk you out of getting a boat. Life is too short and unpredictable.
Good luck, happy hunting.
 

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another thing that is rarely discussed is how well the people on your boat swim.

If you boat from June-Sept, cold water is usually not a life-threatening issue (Great south bay). But, if your wife or kid can't swim, then they can die in 2 minutes if they fall over from a wave rocking the boat. Life preservers on all kids all the time. Swimming lessons for kids (and you and the wife if needed) every year if you are a boater in my opinion.

Get the smallest boat you can that still offers high gunnels with enought freeboard. Usually 21-24'.
 
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