I have an '84 27 that I bought 5 years ago. I'm writing to you on the 9th day of a 12 day trip in the central North Carolina area. I'm in Oriental tonight. First let me say I love my 27. I'm in a marina with about 10 other boats, all over 35 feet and my 27 looks so small, but today on the Pamlico Sound, sailing at 6.5 mph in a 12 mph wind, we were all equal.
My 27 had a Westerbeke 10 hp when I bought. Boat had not been used for several years and water had gotten into fuel. Long story short, I replaced engine 3 years ago with a new Yanmar 15hp - best decision ever! Over the 5 years of ownership, there have been a number of small issues to deal with, but these all delt with wear and tear. I have only a few small blisters, no mast plate problems, minor leaks around toe rail, but I fix every few years. One issue I dislike is bildge is very shallow and below floor interconnections for moving liquid to bildge are inadequate. I have yet to find bildge pump to kick on early enough or shut off late enough - so bildge is usuall loaded and if sailing, water moves to under salon seats and gets anything storred wet. A pain, but not a killer.
I've put nearly 500 miles on this trip staying in anchorages 9 of 12 nights - go for it!! Tony