If you have a couple hundred bucks, you can have a dealer run through it, do a compression check on the engine etc. The last 2 boats I bought (both were in other states from where I live), I did this. Still isn't full proof though.
Otherwise, I would look for the following:
-Any weird discoloration in the gelcoat (may indicate past repair)
-How does the engine look? Check the underside as well for excessive rust. Are all the hoses connected? Check the oil level.
-Can you do a fake a lake test? If so this is helpful to see if rpms stay steady in idle. Does the temp run steady once warmed up? Any weird noises?
-Do all the switches/lights/stereo work?
-What shape is the interior in (any tears, has the vinyl become brittle)
-Whats the trailer like? If grease bearings, is there enough grease in them? Are the ties matching? Are they in good shape?
-Ask maintenance questions like others have said. How many hours used per year? How many between oil changes? How was the boat cleaned? How regular?
Beyond all that, I look for listing that have transparent information. Does the owner acknowledge the pros and cons? Or only the pros (red flag imo). Almost every used boat has an imperfection somewhere, especially if 15-20 years old.
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