"To repeatedly to the same task- over and over, again- and expect different results"
I would have said we are expecting the same results, not different. The result is a safe take off and landing; anything else is not desired.
With the greatest of respect, Nick, I suspect that there is one key difference that may be skewing your perception of the problems. You have had a very diverse career with a range of demanding projects that have stretched your intellectual and cognitive skills. You have been part of a stimulating and interesting team working with cutting edge technology, and you have operated a/c up to and beyond their flight envelopes. In fact, you have defined their envelopes. No doubt, some aspects have been a little mundane (relatively) but probably not for protracted periods.
The average line pilot on offshore operations is carrying out a very repetative task with very little scope for stretching his brain. He may have little or no aspiration to extend himself beyond the minimum required to do the job and, indeed, there may be very little scope to achieve this even if he wanted. The same must be true of Airline Operations. Combine this with unsociable working hours and a potentially fatigueing roster, and there exists the potential for that classic condition caused by low arousal levels, TIBMIN: Thumb in bum, mind in neutral.
Whatever howls of protest that comment might provoke, it has to be acknowledged as a truth, and any offshore pilot who denies they have been in that condition at some point on a flight is probably being economical with the truth (or doesn't remember, because at the time they were TIBMIN!)
So, by all means introduce new technology; I'm a big fan of it as anyone who knows me can vouch. I want EGPWS, TCAS, 4 axis APs, EFIS, FMS. I want new IFR route structures and approach procedures. If you can warn me of wires or that my tail rotor is too close to the crane boom, that's great too. But,the overiding and dominant factor has to be the crew and the way they are trained and the way that training and assessment continues.
Strong SOPs, and crew discipline have to be in place combined with a company culture of expected standards. Do you have a crew that when the "minimums" EGPWS aural warning goes off responds with "200 ft, visual with the runway, landing" every time it goes off, even when its CAVOK and they have seen the runway miles away, or do you have a crew that selects a lower minimum setting, in contravention of SOPs, to avoid that irritating noise. Or that sets a radalt bug to zero to avoid that irritating orange light. Do the crew behave on the line in the same disciplined manner they do in a LOFT exercise, or is that all just for show and, hey, this is the real world. Do you have a crew that's happy to sit at 1850 ft rather than 2000 ft because the pilot can't be arsed to correct the error, and they are hot and tired and busy having a bitch and moan about the company management, or do you have a pilot who curses himself because he has lost 50 ft and corrects immediately? Standards, pride in personal standards and discipline are the corner stones of professional aviation.
However you wrap it up, if you lose 2000 ft and hit the ground/sea, without having noticed it, you are either incapacitated or TIBMIN. Full stop.