Seems unusual that they were "doing the guy a favor" to sell his boat. It would surprise me if they weren't getting at least 10% as a sales commission.
Since the average markup on new boats is in the 30 to 35% range it is no wonder they would rather have you buy a new boat.
Since the OP will need a mainland boat slip if the purchase of island property is in his future I would put things in a different order. Buy a boat slip in a marina such as Mountain View and then buy a boat with a cuddy cabin and spend weekends and vacations on the boat until you are ready for the purchase of island property. That way, when you are ready to buy your dream island house the other necessary things will already be in order.
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