Do you actually think it is feasible to make money on the transaction? I'm curious, not knowing the California market. I've heard that boats sell for higher prices there, but .... You will be spending money to make it ready and to add safety features. Generally speaking, I think that you will be paying retail for everything you put into the boat and selling everything that is new at wholesale or depreciated price. I can't see where your sweat equity will actually improve the basic value of the boat.
That said, if your goal is to use the money from the sale of a 27' boat to purchase a larger project boat, it probably makes better economic sense to simply save for the larger project boat. I think that most of the money that you put into an old, worn boat is done mainly for love of the boat, and not even close to being economically sensible. I've done it, as have hundreds of people in this forum. We didn't do it for the money, that's for sure!
The sail down the coast sounds like fun, and it sounds like you want a good excuse to do it. I wouldn't do it in a 27' boat. In my opinion, it would be more worthwhile in a larger boat, once you have the money to put into it, also with improvements that YOU will enjoy (not the new purchaser -they'll buy it from you at a discount price).
That said, if your goal is to use the money from the sale of a 27' boat to purchase a larger project boat, it probably makes better economic sense to simply save for the larger project boat. I think that most of the money that you put into an old, worn boat is done mainly for love of the boat, and not even close to being economically sensible. I've done it, as have hundreds of people in this forum. We didn't do it for the money, that's for sure!
The sail down the coast sounds like fun, and it sounds like you want a good excuse to do it. I wouldn't do it in a 27' boat. In my opinion, it would be more worthwhile in a larger boat, once you have the money to put into it, also with improvements that YOU will enjoy (not the new purchaser -they'll buy it from you at a discount price).