It's easier to start off with a reef and shake it out, than to raise the main all the way and THEN put a reef in - at least mentally
We have only one FIRM rule
on reefing that is conventional wisdom, "If you ask yourself, 'should we reef?', the answer is 'YES'!"
FWIW, we sailed upwind from Ensenada Honda
, PR to St. Thomas today. Single
reefed main with self-tacking jib
, lumpy, bumpy seas. Dropped the daggerboard to 5'. Winds 18 - 22, G26. Started to put in the 2nd reef when the AWS climbed over 25, but then we got in the lee of St. Thomas. 7 - 10 knots boatspeed on starboard tack and 5 - 9 on port (more directly into the waves).