The first thing I'd do is check the oil. Pull the dipstick and see if it's nice and clear. If it's good after the winter, chances are they cared enough to change the oil. If you're not familiar with other things, here's a simple list.
1. Check the bellows in the stern dirve. Look for signs of wear, cracking or even tears. If it looks weathered and a bit old, replacing it could save your boat from sinking. Not a free job, they should do this as part of the deal if needed.
2. Does the steering seems smooth and without too much play?
3. Does the trim work smoothly, without too much noise, and is the boat responding well to it.
4. Do all of the instruments work?
5. How does the prop look? Any dings or corrosion? Those duo props are very expensive.
6. Are the storage areas under the seats clean and free of water (or water lines and crud).
7. Look under the gunwale storage areas and with a flashlight, follow the wiring around.
8. Is the bilge area clean?
9. Is the engine fairly clean, and free of oily substances that could indicate leaking?
10. Ask about the impeller, and if they don't know, have them include replacement in the deal.
Lastly, miscellaneous. Do the boat covers look and fit properly? Any tears or missing snaps and the like?
Things like the battery can provide some other clues as to prior ownership. Any signs of corrosion? Is it new? Do the cables look pretty solid?
Lastly. Check the seals and strips alongside the gunwhale. Is the rub molding secure? Any signs of damage to the hull's bottom?
Frankly, I'd have a professional surveyor check out any used boat that I looked at. $300 or $400 could very well save you from a bad deal. In addition, a professional survey is a very valuable thing to have if you can get a stated value insurance policy.
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