I had a cruiser in the 90's that ran great and overnight the bilge was full of engine oil. BIG MESS!!!! The problem turned out to be that one stringer was dust. This allowed the engine to sag just enough for the oil pan to be punctured by the jet shoe. The bolts that were used to set the shoe didn't have heads on them, and were a little long. I had no idea the pan was in the danger zone. You bet I ground those suckers down after I replaced the pan and stringer.
SCJB iPhone