Welcome Jeff, Something to keep in mind is that a 40 is almost twice as much boat compared to a 34 or 35 (18000+ lbs rather than 10000 or so. Everything is bigger, heavier and more expensive. And it can also get more complicated to sail - does it have running backstays? I think that a 38 such as Ocean Phoenix does have running backstays - not sure about the 40. My 34 does not. Not a big deal for long passages, but we tend to go out to tool around for an evening tacking and jibing a dozen times in the process or go sail around the islands outside of Marblehead and Beverly and I would prefer to sail rather than motor whenever possible if there is any wind (which is why it is nice to have a light C&C that will move in light air). Dockage, hauling and winter storage all scale with length too. If offshore passages are your plan then the bigger boat is likely a better choice and you want to pay attention to the stability numbers as well, and a C&C may not be the right choice at all (although I am sure there are those on this list who would differ).
Any 30-40 ft keelboat boat in the under $20000 sale price range is going to need a lot of TLC, fiberglass work, paint, rigging work, sails (likely at some point) and replacements over the coming years. We have a 34 KCB and it is a nice size for us and is easy for my wife and me to handle (we don't have or fly a spin although I am looking to add an asymmetrical at some point). If I was to do it again I might look for a 34+ or 34/36 which is a little larger and has a newer style interior layout with a separate shower from the head I believe. While that would have been more money up front, but as I put 10+k into improvements plus lots of time each year it would not have made a big difference in the long run. My boat budget ends up around $20/year, about half of which is slip, hauling, winter storage and insurance, and the other half is maintenance and upgrades. The first year we had the sails cleaned and repaired for $600, had the prop rebuilt for $500, new water heater, new head plumbing, new bilge pumps, new foam for the cushions (which I restuffed myself, etc.), etc. etc.. Last year we got new cruising sails for $6k and some new lines, new water pump, inflatable life jackets, etc.. This year it was quite a bit more (I haven't kept track) because we had the rod-rigging re-ended and needed a new furler and I repaired soft spots in the deck, repainted and refit the entire deck and included replacing winches with self tailers and added a custom bow roller I designed and sent out to a machine shop along with a new anchor and rode. I am glad she is only 34ft long rather than 40! Can you do it for a bit less - yes likely - but it is also nice to be able to improve things and make them better suit your needs and be prepared for the furler that breaks and isn't repairable type expenses. Slip and such are probably a bit less up in Maine than in the Boston area, but it all adds up. Actually from my experience, and what I have read/learned since, you are much better off spending more money now to get a boat that the previous owner put a lot into upgrading and fixing then a previously neglected boat like I did. Like you we wanted to get into a 30+ ft cruising boat at the low end of the price point (we paid $7500 for Wisper in 2018) and I do enjoy working on it almost as much as sailing so there is that. Initially this approach is tempting with lots of old neglected boats in the market, but I wouldn’t likely do that again now that I am into "big boat" ownership. I would likely still get a 40 year old boat again if/when it comes time to upgrade, but I would look for one that someone else did a lot of upgrading on recently and happily pay more for it (there will still be plenty to do and change over the years). On the other hand, I am learning a ton as I try things on this boat and learn what I like and don't like and I am not sure if we would have bought a boat at all if I had proposed a larger budget to my wife initially. And there is also satisfaction in bringing a good boat back from the brink of the scrap yard. Anyway, that is my two cents. Good luck! Nathan - - Nathan Post S/V Wisper 1981 C&C 34 KCB Lynn MA
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