An interesting dilemma to be sure and one we can relate to. When we bought our current boat we had not yet sold our last boat. That was not a happy circumstance and the lesson we learned is to sell first, then buy.
Now we face a new challenge. We would like to buy a bigger boat. Since we live aboard, how do you sell a boat you are living on? Our broker says we need to move off the boat, empty it out so it shows pristine, sell it and then buy a bigger boat. He said that very few buyers will look at a boat being lived on with the same vision as one that is showroom empty. Such problems we boaters have!
1996 Grand Banks 46 Europa