While I'll try not to be too much of pointy headed academic, here is the perspective of an economist (and not a Keynesian by the way). If you are trying to determine the market price for a boat, rather than what it is worth to you (economist's call the maximum price you will pay the reservation price), then you need to determine the prices that comparable boat sold for. This is easy in the new boat market because you can get a true apples-to-apples comparison by looking at the same boat from different dealers. It is more challenging in the used boat market, because it's very unlikely that you will find boats that are qualitatively the same. Old boats by definition are going to have different maintenance histories, more or less wear and tear, and of course some come with more bells and whistle's than others. When I was searching for the O'Day 25 I bought last year, I started the search by trying to get a feel for the market price. I went to lot's of web sites and looking at the asking price and the sold price. I looked at quite a few 25's over the course of a couple of years. This allowed me to develop judgment as to what a typical market price would be for a boat of average quality, high quality, and low quality (given the bells and whistles it does or doesn't have). Note that these prices varied depending on number of factors besides quality (e.g., was the seller highly motivated? Was it sold at the beginning of the season or at the end of the season when the owner may have to incur storage costs? etc.). As an aside, it sounds like you have at least a feel for the market price because you said that your gut feeling was that both are a bit overpriced. Keep in mind, asking prices are almost always higher than selling prices.
To determine the best deal, you have to compare your reservation price with the selling price, and you won't know the precise selling price until negotiations are over. But usually you can get some feel as to how much flexibility there is in the price by just tallking to the seller. I would define the best deal as the one in which your reservation price exceeds your estimate of the selling price by the greatest margin with one caveat. You also need to factor in the cost of updates/repairs that are needed to get the boat up to an acceptable level of quality.
So this is pretty long-winded (academics have that reputation), but I do have one last observation. The asking price for GD is almost 42% higher than for BD. That's a pretty big spread in my opinion given that both appear to be in good shape. I would certainly point out the difference to the seller of GD to try to gain some concessions if you decide to negotiate with that seller.
Finally, although my own reservation price would be lower than either of these two asking prices even if I were in the market for an O'Day 26, Ed is right that that is irrelevant. But that doesn't mean that you ignore whatever signals you can get from your assessment of what the typical market price for a boat of similar quality would be. If the selling price is higher than the market price, the seller will have a hard time selling it. Might they find some buyer with a high reservation price? Sure, but the higher their asking price, the fewer potential buyers they will have and the more likely it is that it will sit unsold. So if the boat has been on the market for a while, that's a signal that the asking price is quite a bit higher than the true market price. Anyhow, good luck with your search. I hope you get a great deal.
Oh and by the way, Ed's also right about Keynesians.
Dave
O'Day 25