I can see dark water (more wind) out on the right, but to get there I have to tack onto port and duck two starboard boats. Is it worth the price, or should I stay with the fleet?

Usually yes, if the pressure is clearly there. Ducking two boats costs about half a boat length, and she ends up a full length behind the first one. Then she is in the pressure: same boat, more wind. By the time she tacks back she is level, and at the top of the beat she is almost a length and a half ahead of both. You must keep clear of starboard either way (Rule 10). Pay only if the pressure is clearly there, close enough to reach and big enough to use. A small patch far away just eats the boats you gave up.

📖 Want Rule 10 in your pocket? The Racing Rules Companion 2025-2028 is a spiral-bound quick reference to the current rules. (affiliate link)

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Next on this shelf — The Upwind Beat