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When to reef may also be a function of who is onboard. Newbies can get freaked by any heeling. If you wish your friends would continue to sail with you, reef early.
Some boats also have tables for optimum heel angles. Downwind, you want to be flatter than upwind.
You might also consider moving railmeat around. Get the crew to windward on a close hauled / close reach, that will flatten the board and reduce weather helm. Going downwind get the crew aft.
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