I would think the items you should look at are pretty much normal items.
1-- general condition of engine -- oil smoke at startup? odd noises? smooth running? hard to start? --- if possible a warm compression check is best ---but sometimes difficult to do when just buying the boat.
If you can pull plugs and look at compression -- look for evidence of rust on middle plugs --possible evidence or riser leaks into exhaust.
Perhaps look for milky color on oil dipstick? -- pull oil filler cap and look for chocolate milk type of residue or evidence on no oil changes -- sludge/carbon etc.
2 -- shift it and check for excessive clunks -- check oil level in drive -
watch prop rotate and look for wobble -- evidence of ben prop shaft maybe
3-- check dashboard electrics to see if most (all) things work.
4-- not sure about that year of Four Winns and wood in floors stringers -- looking for soft wood is always an important thing.
I have a similar but newer boat -- email me if specific questions come to mind. The 5.7 should be a great engine in that --- mine is -- but with DP
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DaleG -- West Palm Beach FL
2003 240Horizon -- 5.7Gi -Duoprop
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