I can easily see how signing a message from a Bitcoin address might seem daunting and complex to those who have never done it before. So my question is this; couldn't an automated way be implemented? In order to sign a message from a Bitcoin address, all that is needed is a private key and the address. The output would consist of the signed message and perhaps a timestamp for added security. How might something like this be implemented in pseudocode?
You can easily do it programmatically with this bitcoind/Json-RPC command:
signmessage <bitcoinaddress> <message>
The problem is you need the private key to do that so it wouldn't be secure at all to implement an online service for this. An offline service wouldn't make sense because wallets already do that. Can you explain better an use of case your proposing?