Join Date: Feb 2000
Location: Annapolis, Md
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Re: Another Boat Buying Thread
Probably the first boat that comes to mind is a Wauquiez Hood 38. These boats meet most of your criteria except age and only slightly on price. (Mark 1's seem to sell for a little less than $50K and Mk II's for somewhere near $60-65K)
A similar boat is the Hood designed Gulfstar 40. They are pretty rare, and a little less quirky.
Hughes- Northstar made a very nice 40 foot mid-ship cockpit design that was a S&S design. These came in a number versions with different keels and rigs. The version that liked best is the cutter rig with the Brewer notch style keel. These are pretty race but an acquaintance picked one up for around $60K roughly 12 years ago so you might find one in your price range.
I also would suggest that you might be able to get by with a Pearson 386. They do have a quarter berth but its partially into the main salon and can perhaps be modified with removable bulkheads to provide a modicum of privacy. They seem to sell for around $50,000 and so are a bit over your budget. A Pearson 385 might also work for you, and it does have two cabins, but I am not a fan of midship cockpit layouts on boats smaller than around 42 or so feet. The shortcoming of the 385 will be lack of storage and motion comfort.
Those are my first thoughts. Lunch is done and I need to get back to work.
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Curmudgeon at Large- and rhinestone in the rough, sailing my Farr 11.6 on the Chesapeake Bay