Re: Newbie questions after first time taking out sailboat
Do you have a topping lift? If so, you need to loosen it when the sail is up so the leech of the sail carries the weight of the boom. Otherwise, you're going to have slack in the sail. That being said, you may have slack in it merely because it is old and stretched. If that's the case, then you'll want to replace it, but how soon you do so is up to you. In many cases, you'll see performance issues with blown out sails, but the boat will still move along OK. She won't point as high, and you'll have trouble getting an optimal sail shape, but as long as you're OK with this, you should be OK for a while.
As to the leak, a cup or two doesn't sound like much water. It may be coming up through the centerboard trunk, and "merely" splashing out the top and into the cockpit. To look for leaks, dry the boat out, then drop her back in the water, but tie her off somewhere. You could try getting some of the blue chalk that they use for "chalk lines" and making some light lines across the boat at regular intervals. That should help you find the source of the leak. But I'd check a few common stress areas, such as around the CB trunk and along the transom (especially near the gudgeons). It's also possible that the drain plug has an obstruction (debris) that allows it to slowly leak.
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1980 Allmand 31
1975 Albacore 15
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