Used to call it the "flinch test". If the reaction to your FIRST bid is not an obvious one, you are too high! All kinds of cautions though. Some folks will get offended and end discussion, so if its a boat you really want, be a bit more cautious. Also don't try to "steal" every boat, but if the boat has been for sale for a few years, its worth a shot. If its a Bristol condition Hinckley, be honest and say its way out of my price range, I cant afford more than Y. It might start a conversation. A couple of examples, my Mariner 28 was listed for $12,000, had been taken by the yard for non payment of fees, and was not producing income. I bid $2700, expecting a counter around 4,000 but they sold it to me. Not as great a deal as it looks. There were some odds and ends I should have included in the sale, but didn't and cost me another few thousand before I got it in the water. I will spend over 10,000 by the time its the way I want it, but a lot of it will be new and the way I want it. A friend bought a Catalina 30 for around $4000 and a Ranger 33 went for $500.00 (no sails)! "abandoned" boats may need a lot of maintenance. But if you are careful you can be sailing a great boat, and fix it up as you schedule "maintenance". Its a lot like poker, and a lot depends on the interaction between buyer and seller or buyer and broker. If you've been looking all this time, and I mean looking at physically boats, not just reading ads, you've got a good handle on the market. Have at it! Good Luck!