All you have to do is setup the cloakcoind on your VPS, wwait for the blockchain to download and copy your wallet.dat file! that's it!
So, out of curiosity, how secure is a VPS? Is there anything that would stop the VPS company from taking the CLOAK and claiming the server was hacked, or is it just really important to be sure to use a reliable vendor? Im in a similar position to as @adamsworks and have considered the same, but Im a bit paranoid about the security.