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I would say start with a 30' or less to start. Get a feel for what you like in a boat then graduate to something else in 2 years. You will soon figure out what you like and don't like. Start cheap then work up.

Starting in the 40' club may be a shock to you financially. Many people don't realize that costs go exponentially as you cross the 30' mark. Marina/parts/sails........
 
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