Re: wind conditions and reefing
Cruise w/ your sails set for the gusts. Racers set their sails for the consistent wind and just deal w/ the gusts.
Singlehanding I am very conservative and don't hesitate to reef or even double reef at the dock before I even raise the sail.
But first I'd find someone to go out sailing w/ you on a day like that and see how the boat handles and reacts to gusts. EVERY boat is different and even the same models can be different depending on how they are laid out and how much load they have.
AND... reefing is just one option (and usually the only option some sailors think of). You can tighten the cunningham (or the halyard if you have more room to raise it), tighten the outhaul, vang and sheet and use the traveler... lots of options if your boat has all those pretty little strings to pull.
CS 36M DIANTHUS