My 265 was 12 years old when I bought it, so been there...
First and foremost, get a high quality survey done... Make sure they are thorough in inspecting thru hulls and transom for water intrusion... Check the tanks for leaks, condition of hoses, yada... Obviously, check the engine compression, exhaust corrosion, etc. All the systems need to be checked - hot water, genset, pumps, etc... Get in deep and dig around... As long as the hull is solid, the engines check out, and the systems are functional, no issues with the fuel tanks, etc., things usually turn out OK... Always good if you are able to get a sense of what the ownership/maintenance history has been... If someone were to buy my boat, I would be able to tell them anything they could ever want to know, because I am meticulous and I do all the work on it myself... Good if you can find one owned by an engaged, conscientious seller... But always hire a surveyor and dig in there...