Mark, Proabably the first thing to look at is how the boat was maintained. If the boat is dirty, and there is a lot of junk laying around that is going to give you a clue that the boat is proably not in the best of shape. Look at the keel botls and make sure that are not rusted and badly corroded, also look at the keel/hull joint. You want to check the cutlass bearing to make sure there is not a lot of movment. If you are near your financial limit replacing the bearing can be expensive depending on the boat. Also make sure there is not a lot of play in the rudder. Stand at the bow and the stern of the boat and look down the hull for any indentations or irregularities that might indicate the boat had some structural work done.Check the level and cleaniness of the oil in the engine. Make sure all the electronics come up. Check out eh mast and the rigging. Make sure ther are no fishhooks in the wire and the halyards and sheets are in decent condition. Again, Mark if you find a boat that you are serious about and going to but down a deposit get a good surveyor to go over it with you.Good luckCharlie