You have to have the line come straight down to the boom as well as back to the end of the boom in order for the new "clew" of the sail to be tensioned properly.
Ideally, you want to pull the clew reefing cringle down as well as out towards the end of the boom. Running the line just up to the reefing cringle will give you the out towards the end of the boom, but will not allow you to give sufficient "downwards" force on the cringle. In the case of strong winds, which is why you're reefing to begin with, the cringle will rise and stress the sail where it isn't properly reinforced, often causing it to tear. Saving some $20-30 on the slightly shorter reefing line could cost you $300+ in sail repairs.... not exactly a wise way to spend your money.
PBTW, any grommet through a sail is called a cringle, and the smaller ones at the reefing points are not reinforced to hold the sail against the stress of the wind, but are merely designed to allow you to tie up the bunt of the sail and keep it from chafing itself to death on a longer passage, as Pigslo has pointed out. Also, it is very important to remember to untie these before trying to shake out a reef, or you'll very likely tear the sail.
The two larger reefing cringles at the luff and leech are heavily reinforced to act as the new "foot" of the reefed sail.
One last point...if you're doing a double line reefing system, it is better to tighten the tack reefing line first, and then do the clew reefing line. Pineapple sails recommends against single-line reefing systems because you can not tension the tack reef point prior to tensioning the clew reef point, and that can damage the sails.
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You know what the first rule of sailing is? ...Love. You can learn all the math in the 'verse, but you take
a boat to the sea you don't love, she'll shake you off just as sure as the turning of the worlds. Love keeps
her going when she oughta fall down, tells you she's hurting 'fore she keens. Makes her a home.
—Cpt. Mal Reynolds, Serenity (edited)
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