Older boat VS a new one
To me, the investment in a sailboat evolves through a series of considerations. I see it as a sliding scale that begins with what is the mimimum I really need and ends with what I really want. How far along that scale I can get depends on the amount of the financial investment I am willing to make. Often, for a given make and length, there is little difference between new and old in terms of safety, comfort, cruising performance, and the pure enjoyment of sailing. However, the difference in cost can be monumental. I ventured into the world of sailing with a used 25' trailerable. To that point, it was the best recreational investment I ever made. After more than four years, I sold it for more than I paid for it. I moved on to a used 30 footer. That was a great leap in creature comforts and also a great leap in seasonal storage expenses. After fourteen years I just sold it for more than I paid for it. To that point, it was the best recreational investment I ever made. Now, I've got a used 38 footer. At every stage, I was either unable or unwilling to buy new. I do not view this as a negative because in each case, I was able to find everything I needed, as well as everything I wanted, at a price I was exceptionally pleased with. I can't imagine how I could have been happier, in any sense, if any of the three boats had been new. But, as with so many things in life, one size does not fit all. People do what they believe is best for them to do at the time they do it.
