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I'd e-mail 4 winns and find out if they were still using plywood cored decks and transoms on that model for that year. If so you have to carefully inspect for a flexing transom and flexing and rotted deck. Does it have carpet glued over the plywood deck or the full fiberglass liner (Better, carpet is BAD in boats). Signs to look for:
Deck--> loose mountings for front and rear seats. Any flex on the deck when you walk on it. Brown stains where screws are put into the deck to attach seats etc.
Transom-->any cracking around the transom mount for the outdrive. Put a pair of thick gloves on and grab the outdrive and try to flex it, the transom should not flex at all. Go in the engine compartment. Look for brown stains or black areas on the inner side of the transom. If the boat takes on water during your water test (check carefully for this) there are multiple causes but one could be a rotted transom that is soft enough that the transom seal does not seal any more. Still in the engine compartment, look at the engine mount pads for cracked fiberglass, or signs of repairs around the bolts that hold the engine mounts in place. Look for rust round the engine block, pulleys, etc, signs that the boat may have taken on a lot of water. Its common to have some rust there but not an excessive amount.
Look on the underside of the hull for cracks, repaired areas, areas where the color does not match, etc. Look at the rub rail for impact damage, this can cause cracking in the glass on both the hull and the top cap if its hard enough. Sight along the side of the hull for wavy areas and depressions. Check in the ski locker for rotted wood (bring an inspection mirror, look at what you can see of the underside of the coring of the deck, be it plywood or composite.
For the running inspection, after starting the engine (notice if the engine starts easily and idles reasonably smoothly) check the gauges, engine temp when warmed up should be 160-175, volts, 13-14, oil pressure cold idle about 40, hot idle not lower than 20.
With the engine running go back in the engine compartment , with a mirror and flashlight (bright LED one). Look for water leaking from the sides of the engine below the exhaust manifolds (signs of a cracked block) and on the underside of the manifolds themselves (same issue). Any water leaking is a problem. Use you nose, sniff round, should not smell like gas or burning oil.
Running test. Test steering and tilt n trim. Engine should go into gear without noises or clunks. The engine should accelerate smoothly and get the boat up on plane easily. The boat should reach its max rpm when properly trimmed (usually between 4600-4800 rpm). If not it was either over-propped (too much pitch) and the engine may have valve problems if run that way all the time. The steering should not be excessively loose (more than 2" of play) and there should not be vibrations when steering or trimming the drive up or down. Check the bilge after running it in the water, there should be none if there is further checking is needed.
Keep in mind that its a 15 year old boat and if it was cared for right it could be in good shape and need some normal repairs, but if it was neglected it could need repairs that exceed the value of the boat. You need to be careful and take your time. This is not like buying a 2 year old car off a lease; there are many more potential problem areas.
Those are the basics, good luck.....
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88 Four Winns 200 Horizon
4.3 OMC Cobra-4bbl
2002 Walker Bay 10/2012 Suzuki 2.5
2008 Walker Bay 8
1998 Jeep Grand Cherokee 4.0/Selectrac
2007 Jeep Grand Cherokee 5.7 Hemi/Quadradrive II
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