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Re: Buying a 30-40 year old boat - your opinions
I agree with SloopB on this.
The key is to find a boat that is not a wreck. There's a sweet spot. But, just like cars, new boats lose value once they are driven (sailed) off the lot.
Just a rough back-of-the-envelope is that a new Jenneau 42DS has lost about a third of its value in the first 5 years. New they are somewhere around $275K and the asking price for a 2007 model is now something like $200K (and probably getting, at best $180K).
Compare that to a 1985 Whitby 42 I saw on Yachtworld for $55K. Probably in sailable shape. Surely needs some work, but even if you're putting $30K into it, you're still way ahead of the game.
Completely different boats? Absolutely. So, that's a caveat. But my feeling is that a 2007 Jenneau 42DS is a lot like a 2007 Toyota Corolla. Will it get you there? Yep. Does anybody seek out a five year old Corolla? Nope. The Whitby, on the other hand is a classic. It's already lost all the value it's going to lose. If you maintain it, you're not going to lose much on the sale - maybe even, God forbid, break even. Twenty years from now someone will still be seeking out a good example of a "classic" Whitby, but in the same time frame, I suspect the Jeanneau 42DS will be long forgotten.