Fascinating Question
I have had nine sailboats, all new and all loved save two. I've had a Cal 20, a Peason 27, a Ranger 29, a Ranger 32 (racing boat), a Scepre 36, and Hunters 40, Vision 32, 35.5 and 380. I've been sailing the pacific northwest for forty plus years. We've had no children so it has always been my wife and I and two cats.The two boats we DId NOT like were the Peason 27 and the Hunter Vision 32. The reason for the negative attitude on the Peason was because the outboard was in a well and hard to manage. I didn't have the brains to figure out that I should have reinstalled the outboard on the stern. It also didn't fit our needs of cruising and sleeping together. It sailed well but had too small of winchess for the jib. Little things that I could have changed but didn't.The Hunter Vision 32 was like getting married right after a devorce. We had the Hunter 40 but had put it into charter and when the five years were up, I had fallen out of love with it because of all the repairs I had done. I wanted a simpler boat so went with the Vision 32. It had a great interior but I never really learned how to sail it. I could not make it sail well. The other boats we all loved for one reason or another. But they all had problems that we thought that the new boat would solve. But there is another point in why some people like me keep buying boats. It is because our needs change. I went from learning to sail to piloting and wanting to go further in our cruises. Then I took up racing and wanted a boat that had bells and whisles. Then we wanted a boat that we could share with friends. With this last boat, the Hunter 380, we wanted a boat that could cruise a distance, drop anchor for several days and be comfortable. I needed a boat that I could get into the dinghy without falling in. For the moment, this is the perfect boat for me. Am I satisfied? Right now, I'm in heaven with this boat. Doesn't race as well since I don't have a asymetrical chute, but it is a fun sailor.We also have generally done well in trade ins or selling our boats. I like to use other people's money so we've had good boat loans. For the two of us it looks like a boat in the 35 to 38 foot range seems to be in our comfort level.So with footitus, been there, done that, even got a T-shirt. I think the final result should be--if you got to your boat and fall in love each time, you have the right boat. The problem is that we humans are fickle.Happy sailing.