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Reefing before you have to
Reefing is not an admission, it is trim. A reefed boat in strong wind is faster, quieter and safer than a full one, because it heels less and the rudder bites again.

The moment
The old rule of thumb holds: the first time you think about reefing, it is time. The second sign is helm load. If you have to hold against it constantly, there is too much cloth up.
How much
Better one reef too early and shake it out again than one too late. With rising wind the next reef goes in before the front, not in it.
The sequence
Come up or heave to, ease mainsheet and kicker, lower the halyard under control, hook or pull down the tack, then take up the reef line aft and only then tension the halyard again. Keep the order, or the cloth sits crooked and chafes.
Shaking it out
Before you shake a reef out, wait through a gust and judge the trend. Reefing in and out with every lull and every gust wears the crew down faster than the wind wears the boat.
What this has to do with insurance
A sail that blows out in too much wind and a rig that is overloaded doing it are two different bills. On an older boat the rig is the most expensive single item after the hull, and some providers exclude damage to mast, boom and rigging together with consequential loss. That one line is worth more than a premium comparison.