You're going to want to hire both a vessel surveyor and a diesel mechanic to perform a separate engine survey. Most surveyors will add in an oil analysis (often for an extra charge). The surveyor usually defers this to the mechanic if you hire him for the engine survey.
You should be able to see obvious issues, like weeping holes in stringers, delamination etc. A surveyor will get into sounding the hull and taking moisture readings. You could buy yourself a moisture meter and take it with you to hit stringers around holes, cuts and bolts, as well as the deck around cleats, rails and rub rail.
Otherwise, just go system by system and look at it. Having had a few boats, you should be able to notice what is stock, what has been DIY, what looks old vs new and whether it look like the DIY work was done by a hack (wire nuts, electrical tape, lack of wire and hose retention).
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