If you've looked around as much as you say, you should have a good idea of what the boat you like is worth to you. Offer perhaps 10 to 20 percent less than that - using information like how long it's been on the market, how eager the broker or selling seems, and all the other points you mention. You're not worried about hurting the seller's feelings with a low offer. Maybe he's desperate to sell before his daughter gets married, and you'll be doing him a favor to give him half what he's asking. You don't know. If he's interested in selling, he will give a counter-offer, and you can go from there. If there's no counter-offer (not likely in this market, but possible) make a better offer. It's a business discussion. At some point, there will be a price
he'll agree to. Hopefully it will be one you can afford.