My 2 cents: If safety is an issue, such as wave sailing in front of serious rocks, then replace sails before they break. If safety is not an issue, such as in my flat water sailing, then replace sails only when they no longer do a good enough job (which for me is after several repairs with tape). I do save some racing sails to use only for races or training for races and I use older sails for general windsurfing. The sails in the worst condition get used for land sailing.
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