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If you trailer your boat, you may want to consider setting up your reefing lines so that everything stays on the boom. The down-side to running a number of lines aft to the cockpit is that they have to be re-threaded during the rigging process. While Redwing has all the bells and whistles and is impressive under sail, she is not notable for a quick rigging time. I believe Judy keeps her stored with the mast up and rigged.
Another issue that has to be attended to when rigging from the cockpit is the sail slugs. Typically the bottom one needs to come out of the slot when putting in a reef. I think Judy had a workaround and it is also possible to just not put the bottom slug in when rigging. A mast gate is a proper solution, but usually requires a bit of hand fabrication to make a closure that fits the opening in each particular mast.
Personally, I question the need to bring all these lines aft on boats where the mast is so close to the cockpit. I've found both of my boats very quick and easy to reef while in the "heave-to" configuration. I actually removed the hardware that the previous owner had added to bring the main halyard aft because it was extra hassle when rigging and I really only found it useful when raising the sail. For reefing or getting the main to come down it seemed I always ended up at the mast anyway. Even on the Catalina 320 I sail on occasionally which has everything led back to the cockpit, single-line reefing, Dutchman flaking, etc. etc., more often than not, someone has to go to the mast to free something, yank on the luff to un-stick a slug, or get a fold back on the correct side. To each his own, of course, but I do have to say that I've drilled holes and added hardware that I later regretted (the holes anyway). It seemed like the hot setup at the time, but as my sailing skills improved, often the importance of my "improvements" tended to diminish.
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