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Considering upgrading my 1967 Contest 29 with a roller Furler. Is this a DIY project? Doesn’t seem too difficult. Which type/brand is best in terms of jams? Any reason not to buy a used one if it’s working and in good condition? We sail on Lake Michigan out of Waukegan, IL. Any suggestions on a sail loft to recut my Genoa for use with a roller furler?
 

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I've installed a couple of furling set ups and most require slipping the foil over the stay. In other words, you might have to take the headstay off the boat and then hoist it back up with the added weight of the furler. It also might mean redoing the swage on that stay, and lengthening the toggle, or just replacing the headstay if it is near the end of it's lifespan anyway. If you feel comfortable doing that sort of work, then go for it. If not, hire a rigger and have it done. Maybe, if you think you need it, you can get the rigger to do a rig survey at the same time, killing two birds w/one stone.
 

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It's a pretty easy job if you don't mind doing some work at the top of the mast. Would take it as an opportunity to replace the headstay as a safety issue. Some furlers require that you put the wire through with a bare head, no swage or StaLok. You can do a StaLok if you can read the instructions, a swage will require a rigger to install.
 

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The Alado is known for its robustness and simplicity, and the halyard is confined to the furler assembly too, so you won't get halyard wrap.

Furlex makes a good product, esp for DIY as it includes a new forestay and a mechanical terminal - it's a standard swivel-based furler that allows you to adjust halyard tension conventionally.

You do need to be comfortable with setting up a temporary stay (halyard) and removing/replacing the headstay - and working aloft - unless the mast is down.
 

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i did the harken single track furler for my 26ft, was an afternoon to install and test. I just had the hanks removed from my geneoa and the #6 bolt rope installed a couple weeks prior to install so i had it ready, after testing i ordered new foresail 135% and enjoy how easy it is to singlehand it.
total cost was around 800 for furler and sail rope modification
 

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Barquito
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If you don't normally store with your mast down, this would be a good year to take it down to do this work. If it has been a few years, it is a good opportunity to take a good look at all the rigging.
 

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Just installed a Facnor. Was not too difficult. Had a new forestay made and installed the furler over the stay and then hoisted it up to the masthead and swapped it with the old.
 
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