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My Island Packet 380 is a cutter and is set up for single-handing. The key is to be able to handle everything from the safety and comfort of the cockpit.
All three sails can be furled/unfurled from the cockpit. The staysail boom is a Hoyt boom, which is self-supporting and thus doesn't require a topping lift. The control line for the rigid boom vang on the main is led to the cockpit. The anchor windlass has a rocker switch on the steering pedestal, so I can handle the anchor from the cockpit, too. An autopilot allows me to do all the sail handling while the boat steers itself, including tacking or gybing. The IP380 has a fairly large aspect ratio for a cutter--I think it sails pretty well in most all conditions.
As far as costs, the boat came that way, with the exception of the rigid boom vang ($500), and the autopilot with 10 meter wired remote ($5,200 installed).
For me, the cutter rig is ideal since most of my sailing has been offshore and in the tradewinds. I added a cruising spinnaker which made sailing in the light winds on the Chesapeake a lot more fun. Again, with a sock for the spinnaker and using the autopilot, I could set and douse the sail by myself.
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