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It is really tough to get a good analysis of a boat. On a car you can at least take it for a test drive, but that is usually not an option when buying a boat. Even if you can get a test drive it will only give you a little confidence in the engine and transmission but nothing about the integrity of the hull.
When buying an expensive yacht it is common to get a hull and/or engine survey. In this situation you pay to have a professional examin the boat and tell you what issues it might have. The cost of a survey is generally based on the length of the boat, usually about $10 a foot but they might have a minimum charge. The surveyor will be able to tell you if there are any issues with the hull, dry rot, improper wiring, etc.
If you live in an area that doesn't have a lot of yachts then it might be hard to get a surveyor. So, things to check yourself:
1) the prop should be clean, no nicks or bends.
2) Rotate the prop, watch the prop and shaft carefully. You can have bend in the shaft so small that you can't detect it by eye and it will cause a lot of problems, so if you can see any amount of wobble in the shaft or prop then it will be a BIG problem. Fixable, but will still cost some $$$.
3) Check the oil in the transmission. Smell it. It shouldn't smell like anything other than transmission fluid. A burnt smell is a good indication of transmission problems.
4) Check the engine oil. If it looks "milky" in color it is an indication of water in the oil, which could be a major problem.
5) Make sure everything works, especially the bilge pumps, blower, ballast pumps, etc.
6) Open every compartment and look inside. A few cup fulls of water in the bottom is normal, but a bilge full of water is bad sign. Don't believe them if they say it was from washing the boat....
7) Duck under the trailer and look at the bottom. Big scratches and gouges are signs of running aground, which will cast suspicion on the prop shaft being straight but other than the cosmetic nature of them are not too concerning. On the other hand, if you see any bubbles or "blisters" in the gel coat then either walk away or expect a fairly major expense. Blisters are repairable, but it will cost and if they are where they can be seen it will always be ugly.
8) If you can't go for a test drive at least have them start the engine and warm it up on a garden hose. The boat should start and idle wihtout any issues. The one thing I can't tolerate is a boat that won't start easy and idle.
9) Consider the recent history of the boat. I would much rather buy a boat that had been used frequently right up to the point it was sold rather than one that has sat unused for a few years.
The frequently used boat will most likely continue on as it did before. If it ran okay before it will continue to run okay. If the upholstery is hanging in there it will probably hang in there for a while longer.
A boat that hasn't been used for a couple of years is a big unknown. If the gas has been sitting for more than a year then it may have degraded and any attempt to use it could really foul up the fuel system. The boat may have run fine three years ago, but now it could have all sorts of issues. Upholstery that sits for a period of time can become brittle and lose its flexibility. If no one has sat on it for a few years it can still look great, but once you start using it may crack and rip the seams very quickly.
Buying a used boat can be a very rewarding experience. While it is possible that you are buying someone else's headache, the odds are pretty good that you are simply buying a boat that simply doesn't fit thier needs. Consider it a good sign if they are upgrading or getting out of boating completely.
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