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Hi Fretbrner,
Welcome to SailNet! :) You've done a great job at outlining your basic needs in a boat, but I have a couple of questions that might help us answer your questions above. The boats you have listed indeed vary a good bit in capabilities and design style, not to mention size. Here are a few questions:

First, where is your proposed sailing area? And related, you mention "bluewater" capabilities--do you mean crossing oceans? Or do you mean hopping from one island to another and along the coast?

Second, are you planning to make those bluewater passages (whichever style you mention above) sooner, or in 5 - 10 years? That could matter too, since it might be worth getting one boat now for local/regional sailing, and a different boat for the serious cruising.

Finally, what type of sailing experience do you have? Can you estimate your skill level? This may help with recommendations as well.
 
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