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Hi NG622. welcome to the world of boating.
I have a seaswirl striper from great oak marina, a 24ft walkaround. it's a great boat for a great price and great oak is a first class outfit. i would definitely look at them. they make a 26 footer with an enclosed head and can be outfitted with twin outboards. it may be out of your price range, but a used one may go for about 60k, as a matter of fact i think great oak has a used one in stock now. i know a guy who has one and uses it for inshore and sharking.
this is my fifth boat, and currently have a larger flybridge. as far as size you'll hear different opinions for a first boat. my first boat was a 30 ft express. i found no problems as far as handling and driving it, it's a matter of doing your homework, learning as much as you can before taking the wheel-like the power squadron course and reading chapman's piloting book(available at west marine and boatersworld). maybe getting a boating buddy or a local captain for a small fee to give a couple lessons once the boat is in the water. our buddy is right, life is too short and unpredictable and with all this water around us having a boat is a wonderful thing. it's a big purchase so be thorough before you buy. best of luck to you.
 
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