Jeff responded to my "New Cutter" thread with the following (edited) request so I have decided to list a few of the major points I used in my own search - I hope someone will find them useful. It's a bit long - Jeff must be contagious.
And now for the request for a favor....We often get new sailors or first time potential boat owners on this site who are looking for a boat and really do not seem to have a clear image of how to set criteria, how to locate the right boat, and what is involved in the purchase process.
My wife & I decided our Columbia 43 was just too much boat for our needs and sold it to downsize. The basic criteria I (we) set out were as follows;
Fiberglass or epoxy composite construction. Around 10K Lbs Disp. Standing headroom in the head. Comfortable cockpit - good seatback height, no sitting on deck with hardware under your butt. Reasonable performer - no Westsail 32's for local cruising. Inboard but no sail drives. Gas would have been O/K if the price reflected it but diesel was preferable. No major projects required. Less than $25K - the lower the better.
Lastly, the boat had to have some personality - the "Row away factor" that is so often missing in the vast fleets of "triangular me-too's" out there. It had to be racy or funky or simply gorgeous but not bland or overly practical - no nautical sensible shoes.
Those were the common criteria. Beyond that, the type of boat was pretty open. I looked at several old IOR racers, a Cooper pilothouse, a Wylie 34, 1/2 dozen Fortune 30's, a Cal 34 and so forth. They all came up short in one way or another.
The Fortune 30 was always at the head of the list simply because of personal tastes - I helped a workmate a bit when he built an early one from a hull & deck and I have always liked them. They also have a proven record of successful offshore voyages so I knew the design & basic construction were sound.
During my search I ran a "Wanted" ad in the local sites - Craigslist, Kijiji etc. but only for a Fortune 30, no general "wants". It was one of the responses to that ad that turned up the boat I finally bought - it had not been advertised.
I used the boat shopping checklist sticky from this site when I found a boat I was seriously interested in. In the end I found it unnecessary though as the boat I chose was obviously a gem - you could see it as soon as you went on board. I know that sounds like hubris but in this case it was true. Sure there are things that need attention but nothing serious or fundamental. That aspect was strictly a personal assessment of a specific boat though and came after decades of working on them and also after detailed viewings of several of the exact same model of boat.
The boat was fully equipped for offshore as well. It needed little other than provisioning before one could set off across the Pacific. Since that did not figure into my plans, I knew I could sell off a lot of the expensive gear like a Hydro Vane and radar to ameliorate the purchase cost.
Since this boat may well be a keeper or "last boat" I really worked at finding the right boat. The whole process took from mid September to early May - probably an average of 4 hours a day.
You can see the results of this process in the thread "Sloops New Cutter".