Potentially all kinds of stuff. Leaks, engine/transmission issues, bent/misaligned shafts, standing and running rigging issues, mast/boom issues, sail condition when canvas spread, etc etc etc etc etc.
Car analogies don't always work with boats, but even if you had a good mechanic look over a prospective used car right there in the parking lot, wouldn't you feel a lot better if you both took that car out for a spin around town and on the highway?
When a closing/settlement date must be scheduled ahead of sea-trial, the customary practice is to place some amount of money in escrow pending sea trial.
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Pacific Seacraft Crealock 31 #62
NEVER CALLS CRUISINGDAD BACK....CAN"T TAKE THE ACCENT