I don't know...the idea of being worth more dead than alive bothers me for some reason, especially if you interject a third party. Do you plan to start sleeping with your one eye open? How would you structure the agreement...the escort gets paid only if you die from old age perhaps, but not if you slip in the shower or fall down a flight of stairs where foul play could be involved? If I had the policy paid up, and wanted to utilize some of it today, I would rather consider a life settlement of some sort (assuming the settlement is larger than the cash buyout). Then I would invest the money and just pull cash out as I need it to pay an escort (or three) if and when the need arises. If you do find an escort that stick with you to the end, you can always leave the remaining money to him by assigning him as your beneficiary for the account (payable on death account). Honestly, 'pay as you go' is probably the only way to go.