whats your boat, and at what wind speed to you reef?

I used to have a Sigma 363 (Mistigo - GBR K714T). Depending on the seastate I found the first reef better than the flattner at about 15 knots apparent.

Current boat is Jenneau SO47 - 1st reef in at about 19-22 Knots apparent depending on sea state. Second reef and roled headail at arounf 26, 3rd reef at 30 then less and less headsail till storm jib and trisail.
 
Twister 28.....I have got a taller than standard mast and masthead rig hence a lot more sail than standard, but it's similar for my boat as the Rustler 36.... no surprises there then!
But in a short rough sea, wind over tide, it's far better to reef early, be more upright, go faster and be more dry and comfy.
Of course it's all about what's due to happen with the wind and possibly if you'r thinking about reefing then you should have already done it.
 
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Slight digression, but if you're carrying a lot of sail downwind, more that you'd carry on the wind, how do you then shorten sail? On your rig can you drop the main without rounding up?

You should be able to hoist or drop the main on any point of sailing on most boats. I do it routinely on mine, a traditional long-keeler of about 8 metres with a masthead rig. Why waste time turning into the wind instead of just going straight into or out of harbour? To lower, top up a bit to support the boom, undo the halyard, and once the luff is slackening off pull in the boom. It needs a bit of pulling on the luff to start with because of the belly of the sail being against the shrouds. I'd be perfectly happy putting in a reef the same way if I had to.

Probably more of a problem with a rig with very swept spreaders and I don't know about down-wind hoisting with full-length battens - does that work?.

When do I reef? She's an old shallow-draft racer from the 1940s and sails fastest on her ear. If there's water on the deck she's a bit pressed, so it was time to reef about 5 minutes ago.
 

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