Re: What to look for? Engine not winterized.
Have the core plugs moved? Look for visible cracks on the sides of the block. Do a compression test.
If he will let you, remove the drain/fill plug on the bottom of the drive while holding a glass underneath to catch the oil that drains out. First thing that will come out is water if there was any in the drive. That could be problematic. Very easy to crack that aluminum drive. Also, first thing that should catch your eye is if he has stored/parked the boat with the outdrive in the trailer-up position. If so, that means an ignorant boat owner, and I would question how it was maintained. Outdrive up in the winter can lead to a cracked lower case.
Good luck!