Someone asked how feasible it is to brute force attack a 256 bit key. Of course, perhaps Quantum computing will change some or all of this, but I am not qualified to comment on that. The thing to remember is that with an encryption as strong as what we are talking about here the weak link should always be implementation. The point is if you info is THAT important there are probably easier ways to get it than cracking the encryption. What you were basically describing in part, as I'm sure you know, is social engineering.
Humans are by nature fallable and are driven by things other then pure logic.
As long as humans still have access to someone's private information, it's never secure.