Since the oil in the engine is clean and the oil in the bilge dirty, isn't it likely that that the oil in the bilge was spilled from an oil change? Additionally, a little bit of oil in the bilge will make a real mess and if there is a gallon of water in the bilge it will be hard to tell how much oil there really is.
IMHO, before you panic and start pulling things apart, you should note the oil level on the dipstick, then run the engine for 30 minutes, shut down, wait 30 minutes, and then measure it again. While the engine is running you should be looking for oil leaks.
Originally Posted by abrahamx
I suppose the crankcase breather is a possibility. It it posssible that the owner filled the oil to half way between full and under full and it has not leaked any oil while on the hard. The oil in the bilge was dirty I am pretty sure. I do agree with the engine appearance. Just not sure how it would get wet being in the middle of the cabin unless it was dripping down the mast. The boat was nicely shrink wrapped. I guess its worth $200 to find out what the deal is.