Join Date: Aug 2009
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you might consider a roller furler for the jib, and running all control lines to the cockpit. It's not as hard as it sounds, though furlers aren't inexpensive. There are some cheap ones out there - but they are cheap. Get a good one, so you don't have to wonder if it's going to work when it needs to (well.. not anymore than any other part, anyway). Also, a tiller clutch (not those tiller tamers... cheap plastic is for walmart, not sailboats) is pretty useful to hold things in place momentarily while you devote two hands to another quick task.
With a furler on the jib and all lines aft, your sloop will be very easy to singlehand (easy is relative.. but you'll get a feel for it). Also, it looks like you have at least one winch on the back of the cabin, so you might already have some or all lines aft.
In other news, what's that rudder doing? There's a lot to be said for having a good rudder. Think of it like an underwater sail. A good one is really handy.. a bad one is harsh.
... or I'm wrong.
Living aboard, currently in the Chesapeake
O'Day 37, still new to us