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There was an article in Good Old Boat last winter on buying old boats. Basically the gist of the article said, figure the lowest possible and offer even less, way less. If the seller wants 20K offer 8K.
Last winter (there was ice around the boat) I looked at the boat I wanted and the seller was aqsking over 8500. I offered $5K. My brother thought I was wasting my time. I went tot he broker and give him a good faith check for $100 and the offer of $5K. Two weeks later I had the boat for $6K. The upgrades in sails and new engine and cushiins were more than that.
You need to know that there is no perfect/must have boat, at any price. Offer as if you can do without the boat, because you can, and offer low.
Joe McCary Aeolus II West River, MD
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