At some point, you will reach a skill level that you will want to own your own boat. I’ve limited the discussion in this post to small sailboats. So let’s define that. A small sailboat would be any dinghy. Like a Laser, Sunfish, Lido 14, Sabot, Lightning, Buccaneer…anything without a keel and that you don’t generally leave in the water overnight.
If you’ve already decided on a boat type, then I would spend as much time as I could researching it. Look in forums and on the Class Association website for consistent “trouble spots.” Often those could even be year model based. You will want to know that a Glouster Buccaneer 18 has a lower mast step than a Nickels Buccaneer 18 and that means that mast replacement (if ever you had to do one) may be difficult. If you haven’t decided on a boat type and are just out there looking for a good deal, when you find one, do the same research. A good deal may not be so good if you are armed with a little more information.
Now, the actual boat. Feel it. Put your hands on it. Push on the sides. Do they flex? Should they flex? Finn’s are notoriously thin-skinned, but most boats should have very little give. Look at your hand. Is the hull super-oxidized? That can be worked on to a point with just rubbing compound but there is such a thing as too far gone. How is the deck? Does it crinkle when you push on it? Especially at the sitting locations. How often was the boat used? I like boats that are used a lot! Their owners usually take good care of them. I’d also ask why they are selling.
What about the rigging? What shape is the mast in? Any dings? Any unnecessary holes? Those can cause failure under load. When was the last time the shrouds were replaced? Shrouds can fail at the fittings on their ends. Pay particular attention to what they look like at the joints. How do the chainplates look? What condition is the running rigging in? Is it in accordance with class standards? You may not intend to race at all but usually the upgrades and the rigging set forth in the Class Rules is a good system and having the most current will add value when you eventually sell the boat as well.
Since we’re talking about small boats, we have to talk about trailers and dollies. Does it come with a trailer or a dolly? Does the trailer have a valid registration and title (if required in your state.) When was the last time the bearings were packed? How are the tires and the spare? If you are buying and driving it home for a distance it would be a good idea to plan some extra time to deal with this if it hasn’t been taken care of lately. What size hitch is it? If it only comes with a dolly, how are you going to transport it home?
Most important thing is not to let your enthusiasm and emotion overwhelm your common sense. The best approach is often to have several boats to consider so that you have an excuse to hold off. I almost always wait a day before agreeing to a purchase. Almost.