I realize it costs nothing to make an offer but would you make an offer on a boat that is priced $10K+ more than boats that, compared to this one, are loaded to the gills? It makes no sense to enter into a sales contract that is not only is listed $10K+ more but that would cost about another $10K to bring up to snuff with the other boats. Not when there's other boats you could buy and save that $20K...
Then why not place an offer on one of those other boats? That's a question you need to be prepared for, because when you make that argument, that's the question a seller or a good broker will ask. If the broker is sharp, he may be familiar with those other boats and know the answer to that question. Have you looked at those other boats? If they're so much better, then why are you wasting your time with this boat?
I don't buy the "loaded to the gills" thing, since on used boats most add-ons add little to the dollar value of the boat. If they have so much value to you, then you should buy the other boat instead. In fact, I'm a little puzzled that you are fixated on this one boat if there are sister ships that are so much better equipped and lower priced.
What I was suggesting is since the broker almost certainly told the seller he was going to show the boat, and since the seller will most certainly ask the broker how it went, the broker might inform the seller his boat is overpriced, compared to what's on the market today. What the seller does from there is his business. It's not my job to show him the light.
It's your job to show him the money, if you want to buy his boat.
I'm concerned that you are assuming that the seller is far more engaged in this process that he may really be. Do you really think he is hanging on every showing of his boat? He might, but some sellers just hand it over to the broker and head out of town, out of the country, etc. Many sellers are the heirs of the deceased owner, and have no connection to the boat other than some idea of how much money they want (and willing to wait to get their price). Some sellers don't really want to sell the boat (spouse making them do it, reluctant to admit their health is declining, etc.), and will continue to use and enjoy the boat until they get their price.
If the boat is overpriced, the broker has probably told the owner before you came along. If you come in with a list of reasons why the boat is a lousy value, he may not see a win-win opportunity.
I'm afraid your expectations are unreasonable if you actually expect him to lower his asking price before you even make an offer. Adjusting the asking price means forcing him to accept a lower offer from EVERYONE, not just you. That could be humiliating to him.
As I advised you before, you should stop being so hung up about asking price, do your homework to determine what the boat is worth to you, and offer that amount with an explanation to back up your valuation. That explanation should be based on boats that have already sold, though. If you use other boats currently on the market to justify your valuation, then the seller is just going to be confused at why you don't buy one of those other boats. Good brokers can tell when you're being serious, and when you're just playing games to lower the price.
...It been said time and time again here, "Buy a boat that has everything you want on it, or as close to that as you can get, so you can enjoy sailing rather than pouring money into her and being stuck in the harbor fixing her up."...
I think you're taking something out of context. A boat that's "loaded to the gills" is not necessarily in sail-away condition. A boat that has fewer accessories but is in sound condition could get you sailing now, and you can take your time adding things that are nice to have but not absolutely necessary.
I think you're confusing the two, and that can be dangerous. Just because you have to buy ice doesn't mean the boat will be stuck in the harbor for repairs. And just because a boat is "loaded to the gills" doesn't mean that it won't have a serious mechanical failure that could lay it up for a whole season. Just ask JimGo about that one.