2. if its encrypted using a easily dictionary brute force attack then its only time before they get to your coins. so i would suggest you use your backup and move the coins to a fresh address, leaving them with a empty address once they get into the wallet.
3. as for the DPR scenario, he should have had a relative entrusted with a backup, and as soon as he was arested and his wallet file in the hands of the authorities, that relative could have used the backup to move the coins to new addresses
In hindsight yes...but I don't think he was planning on getting arrested
In hindsight, being in the USA was crazy stupid. Unbelievable really. He had so much money, and was running such an incredibly illegal operation and attempting to murder people, and he was living with a roommate running his empire from the public library. I mean, it boggles the mind. Obviously the painful truth is that DPR was pretty freaking stupid. Good with computers. But stupid where everything else counts.
So no, obviously his wallet wasn't properly secured. He obviously liked opening up his Bitcoin-qt each morning and counting his coins. Crazy.
Yeah I am sure you are right..he probably felt so gangster looking at his btc balance everyday lol.