Article: Look for chafing, repairs, stretches, pulled-out stitches and broken slides. Mildew is harmless but tough to get rid of. Check spinnakers for excessive bagginess. Hoist the windward sails and check for excessive draft and stretch. Remember that replacing the sails can cost you half the price of an old sailboat. You can pretty much count on replacing a lot of rigging on any old boat, though. Check for worn pins and shackles, unraveling wire, broken blocks, worn-out lines. These items are relatively easy to fix and replace, however. Winches should work smoothly, but if they don't, you can almost always get them running right with a quick cleaning and greasing.
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Take all of the sails out of their bags and spread them out. Rigging will show the general quality of the boat's maintenance. If possible, hoist all the sails and work all the halyards, sheets, winches and furlers.