1) Go for a test ride. While in the water, operate EVERYTHING! Make sure everything works. When you pull it out of the water and pull the transom drain plug, how much water is coming out (does it leak?).
2) Operate the boat at idle, mid-range, and wide-open throttle. Make sure it runs “solid”.
3) Ask what service has been done on the motor and if there are receipts to prove the work.
4) Do a compression test on the motor. Research your motor and find out what the compression in each cylinder is suppose to be, with the tolerance noted. Typically, each cylinder should be within 5% of each other. Generally, as long as each cylinder is over 110lbs, you should be good.
5) Make sure trailer lights work and wheels bearings seem solid. Make sure tires are in “good shape”.
That is about it. It isn’t new, but as long as it is mechanically good, you can’t ask for much more.