A better solution is to just have the sending wallet check to see if the address you are about to send to has been used before. If it's a fresh address, it sends it through without any popup alert. If the address has history going back a certain amount of time, then a popup comes up and notifies the sender that they are sending to a non-fresh address that may no longer be controlled by the receiver anymore.

Also, an even better idea is to set up an "address expiration service". When you delete a wallet, you first send off an "expiration notice" which is just a message (signed with the private key) saying "I am about to delete this address, here is my new address". When someone tries to send to that address, they first consult the address expiration service, and the service will either tell them "this address is not expired, proceed", or "this address has been expired, please send to this other address instead...". Basically like a 301 redirect, but for addresses. I don't think address expiration should be part of the protocol.