Man, wheels within wheels. Are you suggesting that the insurance actuaries have factored in that high-time pilots tend to make decisions so amazingly stupid that no payouts will be necessary, and thus have adjusted the rates downwards for high-timers, whilst laughing down their sleeves?
Example 1:
Corporate flight department contracts two pilots to fly a high performance turbojet aircraft. They are not specifically named on the insurance policy, and therefore must meet the "open pilot clause" specified within the policy.
Captain has 24,000 TT, is typed rated with 3,000 hours in type, and meets all criteria of the clause.
F/O has 1200 TT, is not type rated but has been to FSI, and does
not meet all criteria of the clause.
Captain has been in corporate aviation for 25 years, so is very aware that the F/O probably does not meet the insurance requirements. He questions the aircraft operator about this, but is told to not worry about it. The F/O is a close friend who he is trying to assist in advancing his career, so he agrees to take the trip.
On landing at the destination, aircraft runs off the end off the end of the runway, causing substantial damage. Aircraft is totaled. Insurance refuses to pay out. Why? The F/O was did not meet the requirements of the open pilot clause
and the captain made the decision to fly the trip even though insurance coverage was in question. The operator of the aircraft sues the pilot to recover the value of the aircraft. A 24,000 hour pilot made a poor decision that cost him 4 million dollars.
Example 2:
Recreational pilot owns a 1/2 share of a V-35 Bonanza. He has 6,000 TT, 250 actual instrument and 3000 in type. Pilot plans a business related XC trip in inclement weather. On approach, pilot experiences mechanical difficulty and crashes 4 miles short of the runway at his diversion airport. During the accident investigation, it is discovered that the pilot did not posses an instrument rating. Insurance refuses to pay out, and the wife of the pilot is sued by the family that owned the other 1/2 share of the aircraft to recover the value of the aircraft. She must declare bankruptcy to protect herself and becomes a victim of her husband's poor decision to knowingly fly in IMC without an instrument ticket.
The latter example is a true story.