As an example, if the random number generator that is used to generate the k value when singing a transaction isn't sufficiently "random" it becomes possible for someone to use multiple signatures from the same private key to compute that private key and steal your bitcoins. If you use a new address for each transaction, then you never have multiple signatures from the same private key, so this is no longer an issue.
Forgive the intrusion, but I'm curious, Danny. Do you really discard the private keys once you cleared the unspent output, as you state on your BTC trading post? Or do you keep them in archive wallets "just in case"?
It is safest to assume that I discard them regardless of what I actually do. No harm at all can come from accepting that I discard them.