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My sense about all this is that you are better off focusing on a boat and sea trials on such boat. By the time you are even half way to the various destinations mentioned, things will have changed.
Get your real-time info from cruisers, the nets, etc. and make your zig-zag route adjust based on what you hear and how much $ you have.
It is, after all, all about the journey, not the destination.
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