Can someone critique my current vending setup and tell me if it's secure enough:
The rest of the BTC I transfer back into Silk Road into a buyers account and buy drugs domestically with that I can turn into cash quickly while making a small profit.
That depends on how well you separate your MtGox account from your SR account. Since your real identity is linked to your MtGox account, hopefully you run those coins through a mixing service, or two, or three.
I also have a hidden usb stick... that runs tails, that I boot the personal computer from. I keep a small encrypted file with the Silk Road URL and all login details hidden on an online email account I access through the Tails USB before I go on my Vending account. I also keep a backup copy of my passwords and BTC wallets encrypted on a USB that I have hidden in a family members house that will never fall under police suspicion just incase I lose any of my details or the online email account goes down.
If you read through my post history (I'm a little too drunk to find the posts myself right now, but some of them are in threads on the front page of the Security section
, you'll see that I'm not a fan of encrypted volumes (files, partitions, external media) per se, because they can leak info about their contents onto unencrypted drives, but loading encrypted volumes from Tails is safe, because it is booted in a read-only state and saves nothing, and implements added security featurs like scrambling RAM on shutdown.
I think your set up is pretty safe overall. It really all depends on how strong your passwords are. Remember, the security of a 256 bit AES encryption key depends on the bit strength of the password used to encrypt it.