It's a rare sailor indeed who allows money to be the deciding factor in the relationship of him and his love for a particular vessel. We almost always go the way of our hearts... not our wallets. The love a boat can be stronger than the love of a lifelong mate, i.e. you never feel the need to use an excuse to leave the presence of a boat to get a beer...you actually get beer and bring it to the boat.
And having a boat you love means it's okay to just go sit on it in a marina or on anchor and not go anywhere at all. If the weather is bad or you don't have enough time to take her out, just sitting aboard is nearly as good.
I also pompous-assedly do not agree with those who decide which boat to buy based on its resale value, e.g..."Man I love the lines on that Herreshoff but the CataHuntalina will hold its price better."