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Old 01-01-2008
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By properly setup I think you mean making sure the lines are all led back to the cockpit and that kind of a thing. If not, could you say a little more about this ? I would appreciate it.
This can include things like having all the lines led aft so you can raise, drop or reef the main from the cockpit. On most boats that would mean you'd need the main halyard, topping lift, outhaul, reef clew and tack lines for reef #1 and #2... so seven lines led aft at a minimum. You also might lead a boomvang or cunningham line aft.

The jib halyard can generally be left at the mast, since most jibs/genoas are on roller furling nowadays..

BTW, I prefer a boom brake over a preventer, as they're much simpler to deal with and generally easier for the short-handed sailor to use. In some ways, they're also safer to use, since they do allow the boom to move—albeit far more slowly than it would if not under the restraint of a boom brake. You can generally set and forget a boom brake—while a preventer generally needs to be unclipped before and then re-clipped after every gybe.

You'll also want to consider where the roller furling lines lead back to, since you'll be wanting to be able to unfurl, furl or reef your roller furling headsail from the cockpit.

A good sail to have if you're sailing shorthanded is a roller-furled asymetric or screacher. This sail is exceptionally easy to deploy and relatively simple to use, and provides you with a lot of sail area for light winds. It is far simpler to use than a traditional symmetric spinnaker, with less risk of broaching, but doesn't give you quite as much horsepower.

You also have to pay attention to how the mainsheet and genoa sheets are setup. On some boats, the mainsheet and helm are aft but the genoa sheets are at the forward end of the cockpit—making it a bit more complicated to singlehand the boat. This is especially important on some of the coastal cruisers, since they will often have a larger cockpit than a bluewater type boat will of the same LOA, making the distance from the front to the helm even further. On a tiller-steered boat, you can often get away with this kind of setup by using a tiller extension and leading the mainsheet forward to where you can reach it while working with the genoa sheets. This is something that you will need to look at as it varies quite a bit depending on the boat.

Another thing that helps is how the instruments are setup. Can you see them from where you normally will be when at the helm? Can you see them when you change position from a starboard to a port tack?

Having line controlled genoa fairleads and mainsheet traveler are also good if your sailing short-handed. It makes adjusting them much simpler.

BTW, a small tiller pilot can often be used to steer a boat that has a windvane setup, even if the boat is wheel steered.

I hope this helps.
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Telstar 28
New England

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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