I think the guide to being secure doesn't need to be complex at all, though I don't know if the required technologies are available to write such a simple guide.
For example I think that an offline computer can send money without being connected to the internet. You just use your signing keys(you must also know manually how much bitcoins you have beforehand, without having any blockchain around. Here you can use blockchain.info to check that up, advised to access it through Tor. Then since you know how much you have, you use your private key on that offline computer and sign a transaction. Then you transfer that transaction with a usb key storage to your main computer which may be virus and trojan+keylogger infested and just execute the transaction. Voila!
Though are these technologies available. We would need a very simple program, one that doesn't like need the latest version of Ubuntu, not the full fledged bitcoin-qt, except if it can work in offline mode and it can allow to send Bitcoins without needing an internet connection.
The above are maybe a bit of half-baked thoughts.
The Bitcoin-qt client can create a raw transaction offline with the createrawtransaction command (in the console window), and then it can send a raw transaction with the sendrawtransaction command.
See
https://en.bitcoin.it/wiki/Original_Bitcoin_client/API_Calls_list for a list of commands.
