Chris 249 said..
With your background you may find Compii etc a bit too pedestrian, especially given the big overlapping headsail which will have to be furled in a breeze and therefore inefficient.
For some reason I'm having trouble copying links, but on Yachthub there's a Hutton 28 that could do with aesthetic work down below, but looks good from outside. They're actually a development of a quarter tonner, much hacked about and not beautiful IMHO, but they're not a bad combination of good interior size and decent speed, with a fractional rig to allow easy depowering. I had a mate with a good all-round sailing background who was happy with his one. At $11000 with a decade-old engine and rigging it sounds like very good value, and the lazyjacks, boom bag and fully battened main make life incredibly easy. It looks like a handyman could put in a bulkhead to separate the head from the vee berth pretty easily, which makes a huge difference IMHO. My wife and I aren't fussy but we have found that even a cramped separate head is vastly better than no separate head.
Lots more pace than the skinnier older-style boats, significantly quicker for coastal jaunts, and if you handle it like a dinghy then it could be easier to handle. This particular Hutton 28 used to be a regular in the offshore fleet when it was new so it's not a paperweight even if some of the joinery looks rough.
Personally I find it better to upgrade an interior with timber trim than to upgrade an exterior, which normally requires expensive slip time and can result in either having to pay for a pro or risking a horrendous amateur paint job. I had a 28'er for years; it's a great size of boat because it can fit in all the features of a bigger yacht but you're a ton or so lighter than a typical 30 footer so everything is one or two sizes down and so is the budget and the weight of the gear. We love our 36'er but you can't do things like play the mainsheet when zapping home in front of a big nor'easter in the way you can do it with a 28'er.
I had one built by the Hutton brothers in the very early 80s and kept it for well over ten years. It sailed well (with the optional tall rig) and as you say it had plenty of room inside for the size but I sold it in the end because I didn't trust that the keel wouldn't fall off.
The keel is a hollow steel fabrication with lead poured in the bottom third or half (or probably however much they felt like on the day) with an outward facing flange welded on around the top and bolted up into the hull.
Despite my giving the hull three coats of epoxy before I ever anti fouled it and put it in the water every time I slipped it the keel showed signs of rust around the flange (and elsewhere) and as I didn't think the steel was particularly thick I eventually didn't trust it. When the ballast was poured into the keel it bowed the keel out more on one side than the other so it was not symmetric.
The hull and deck always seemed reasonably solid to me and certainly not what I would call light weight.
My boat has some Italian sounding name now and is still at Clareville on the same mooring I installed. It has been for sale for over two years (perhaps on and off) and at one stage it was advertised that the keel had been redone - whatever that means. The original chain plates were also a bit of a strange set up being bolted to the side of the coach house roof which in turn had an internal stainless steel bracket bolted to the main bulkhead. The main bulkhead was tabbed to the hull but only at its lower portions which I was never that happy with.
Anyway if you inspect these items and it looks solid the boat should be quite good although the timber skeg was not encased in anything waterproof and could be rotting and the thin guage stainless steel rudder was rather wavey and was always full of water.
