When airline flying there is no situation that is not/cannot be trained for.
Really? Seems to have been rather a lot of airliners in the drink over the last few years........
Speaking as a Commercial Pilot, I am pretty sure that we have not trained for every eventuality we just try and envisage failures and train for them.
When private flying, I am quite happy to fly my single Engine Cessna at night, under IFR and across water. We assess the risk individually, if we don't like the risk then we don't take it and I am not going to knock anyone for having a different level of risk assessment to me.
Apart from wearing Nome and a Bone dome in a spam can, which I think is just plain daft....