Some things to check
I bought a used 89 4 years ago, so this is my experience. My best advice is to get a good marine surveyor to go over the boat and engine. He should sound the hull and deck and check the hull with a moisture meter and experience the engine running in the water. Things to look for are movement of the motor mounts, play in the cutless bearing, blistering of the hull, delamination of the rudder, interior stains that indicate leaks, condition of standing rigging (kinks, burrs) condition of the stitching on the sails and condition of the fabric (stiffness and distortion), condition of fuel (should not look like tea otherwise you have bacteria in the tank), oil in bilge, sight along hull to look for glas work (some distortion is normal, tension on the steering cable, tension of engine belts. There will be gel coat cracks but they should not be serious. Hope this helps. The boat has been enjoyable but because this was the first year of this model things were not thought out as well as the should have been, esplecially access to the engine, shut offs, filters and water pump. Good LuckP.S. Also read the "review" on this site for the thoughts of others on this boat