A cat-rigged boat is the simplest to operate, but can be a bit challenging, since you only have one, very large sail to deal with.
Overall, in terms of efficiency and ease of use, the most popular and useful rig is probably the sloop/bermudan/marconi rig—a mainsail with a single headsail.
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You know what the first rule of sailing is? ...Love. You can learn all the math in the 'verse, but you take
a boat to the sea you don't love, she'll shake you off just as sure as the turning of the worlds. Love keeps
her going when she oughta fall down, tells you she's hurting 'fore she keens. Makes her a home.
—Cpt. Mal Reynolds, Serenity (edited)
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Still—DON'T READ THAT POST AGAIN.