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Adding either lazy jacks or a stack pack will make handling a luff bolt rope mainsail much more difficult. Either of those simply make raising and lowering a bolt rope sail way harder.

As others have rightly suggested, the most effective and least costly option would be to have a sailmaker add slugs (slides) to your mainsail. This will greatly simplify raising, reefing, dousing, and flaking the mainsail. The slugs will keep mainsail on the boat and attached to the mast.

That is exactly what I have done with my mainsail. Within weeks of buying my boat, I had slugs added to the mainsail. A few weeks later I removed the lazy jacks because they made single-handing wildly more difficult. My boat has a similar rig to the San Juan 33s, except my mainsail is roughly 50% larger and weighs in a little over 100 lbs.

Based on my experience, once you add slugs, flaking the mainsail solo gets quite quick and easy even for an old guy like me. The trick is to start by 1) checking that each of the flakes between the slugs falls to opposite sides of the sail at the luff, 2) that you have sail ties in you pocket or hung on your neck, 3) that the mainsheet is tight and traveler is hard over to the side that is opposite from the side where the sail is on the deck, and 4) that all of the sail is on the deck on one side of boom.

Then, standing on the opposite side of the boom from the sail on the deck, starting from the clew of the sail make folds that results in parallel folds that line up with the folds at the mast. Once you are roughly a quarter of the way up the sail, tie on a sail tie and keep moving up the sail adding sail ties as you go.

Once you get used to it, your life will be much easier.

Jeff
 

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Or install the slides and a Dutchman system.
I like the Dutchman System for really big mainsails on cruising boats where the sheer weight and size of the sail, makes sail handling a lot more difficult. Conversely, this is a pretty small and light sail. The cost to add the system, and modify the sail and the sail cover to allow the use of a the Dutchman System would be disproportionately expensive relative to any gain in ease of use. I respectfully suggest that with a sail of this weight and size, it becomes just a matter of practicing flaking the sail before flaking the sail becomes second nature and no big deal.

Jeff
 

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I understand what you are saying Jeff. But as a fellow older sailor, I would have a much tougher time single handing my 33 footer without the Dutchman system. I guess I am spoiled.
Jim,
I see nothing spoiled about that. Raising and flaking the mainsail, and spinnaker raises and drops are the hardest things that I do on my boat. I have been very fortunate to be able to do these things at my age and know that there will come a time when I cannot do these things on my own.

My wife is still annoyed with me over an incident that occurred while I was flaking the mainsail during a summer cruise. A really big powerboat wake hit the boat while I was flaking the mainsail. I typically hang onto the boom with one arm wrapped over the boom supporting my weight and keeping the flaked portion of the sail from unraveling. I had not properly cleated the mainsheet, so the boom rocked out over the rail on the side of the boom that I was standing on. I ended up riding the boom out over the rail and then back aboard again. It was no big deal to me...All in a day's work, But as my wife pointed out, "Someday your luck will run out, and you won't be that lucky." She is of course right. I am not in my 60's anymore, and so need to be careful and should not be taking those kinds of chances.

Which is all a long way of saying, I fault no one for taking any measures that makes sailing easier and more comfortable for them as a way to keep sailing as the sand pile gets larger at the bottom of the hour glass.

Jeff
 
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Why do lazy jacks make single handing more difficult?
I think I was the one who said that lazy jacks make short-handed sailing much harder and removed the lazy jacks from my boat after sailing with them for a short period of time.

But my issues were that lazy jacks keep the sail close to the boom, but that comes at the price of a number of inconveniences. During raises battens tend to catch in the lazy jacks. Similarly they cause the sail to bunch up at the gooseneck making it harder to use two line reefing.

Proper sail care requires flaking or rolling the sail. That is much more difficult with lazy jacks in way, and gets almost impossible single-handed.

With the type of mainsail with a bolt rope instead of slugs that the original poster has on his boat, there needs to be a prefeeder a couple feet below the entry port and lazy jacks prevent the prefeeder from working.

Jeff
 
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