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I just bought my Endeavour 42 in May. My prior experience was with a 26' power boat and a one week crewed charter. So far so good. We are on the Great Lakes and have sailed in 30k winds but have not had to deal with big seas or currents. We find the sail handling to be easy for the jib and a bit difficult for the main, but will take care if the issue with the main this winter. I am not intimidated by the size of the boat under sail. Docking it took some getting used to!!!
I was also shopping the Hunter 42 CC of that vintage. I really liked the interior layout a lot. The problem was that all the ones I looked at had a lot of issues, and some of those issues were not easy to fix. My E-42 has a lot of issues too but they are things like replacing hoses and frozen seacocks. Nothing structural or major cost. I have added radar/plotter and a new anchor & chain so there is a bit of cash. I replaced both A/C pumps. I had to add a holding tank that the owner said was there and was missed by the surveyor. But I shopped hard and did the work myself (except the mast install of the radar).
If you are going to buy a boat more than 10 years old, expect it to have issues. When you look over the boat, you'll see things that you'll know need dealing with. Multiply that list of stuff by 5 and that's what you'll be faced with. You'd better be handy with tools or else have a big checkbook. Plan on spending a year in benign waters with close access to parts and repair facilities. Get up to speed with all systems and then work your way into bigger adventures slowly. This ain't brain surgery. But it is more costly and more work that you think it is.
I bought the E-42 over the H42 because I could see the difference in structural build quality.
BTW, the E-42 has an encapsulated keel with lead ballast. Not as fast to windward as a modern external keel but I don't have keel bolts to worry about. When I was out of the water, a new H45 was set next to me. They hit a coral head with their keel and have delamination in front of and behind the keel from the torque applied to the hull. I saw the same thing with a Catalina/Morgan 45. I expect I'll be hitting something sooner or later and will be happy with my keel long after I've been passed by all those 'fast' keeled sailboats!
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