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Re: More what's this rigging questions
What's the coiled line attached to on the other side of the boom?
There should be 2 bails or clips that the bitter end of the reefing line attaches to.
opposite the blocks. I have an eye sewn in mine that attaches to the clip.
Looks like you were set up for two reefing lines. The aft block for the 1st reef, the forward for the second. You pass the lines up the port side of the sail thru the grommet and down thru the block and forward to the cleat. You can pass them thru the bail for your mainsheet if you want to keep them from hanging down, or not, up to you.
If the line doesn't fit thru the block, as Caleb says replace it. It looks old, it's also probably swollen, which may be why it's not fitting through the block.
You can rig both reefing lines, just make sure there's no tension on them when your mainsail is fully raised. Tie them off at the forward cleats. I might use different colored line so you always know which is which. Like Red for 2nd reef..maybe