Ok Rob I'll try to find some bad news items to mention but after 11 years I can say that I really love my boat and I have no need to "move up". My boat is a wing keel, advertised draft id 4'6", loaded down mine might be 4'8". The wing keeled version is 500 lbs heavier.
I changed the fuel pump on my Yanmar last summer, a bit of a pain with the space constraints but I managed it in about 90 minutes.
I haven't yet tackled changing my exhaust hose but I know its going to be a tough job and not one that I'll do on a hot day.
I changed the hinge mechanisms on all of the Lewmar hatches about 8 years ago. They're the kind that are supposed to stay open by a 3 position hinge but none of them did. Lewmar did a part redesign and I haven't had any more problems since I replaced the parts which if I remember right were under $40 per hatch.
My rudder had water intrusion from the top of the rudder post and I got a few hairline vertical cracks also about 8 years ago. I drilled holes in the side and injected epoxy into the voids, I used about 1 1/2 litres of epoxy. I drilled a 1/4" hole at the bottom of the rudder and I leave it open, after haulout it drips for a couple of hours. Eventually I'll get my rudder rebuilt, I got a quote from Phil's Foils in Ottawa and he quoted $1200. if I bring him the old rudder and he re-uses the shaft.
At the end of the day not bad for a 23 season old boat. I club race in the white sail division and we're consistently in the top 3 boats. The type of boats I race against: Corvette 31, CS 33, C&C 36+, C&C 37XL, C&C 34, Elite 364, C&C 29 Mk II, C&C 27 Mk III, Mirage 33.