How do you solve getting to the secluded bitcoind to command it to sent bitcoins out?
IMO, the best solution is to walk a request to the box. You can also have the box connect out to a web server that provides it with transfer requests that then just have to be manually approved at the box. The most common transaction will be to move coins to the cold wallet, so all you need is an amount.
IMO the best solution is this:
https://bitcointalk.org/index.php?topic=92496.0 (Armory on web servers)
Plus an offline wallet to store the bulk of the reserves, not in any actual running computer connected to anything.
http://bitcoinarmory.com/index.php/using-offline-wallets-in-armoryIf etothepi could commit to Bitfloor I'd be all over the IPO with a 100K+ valuation.