Autoresponder AND Delete AND Forward?

Both scenarios fall into the "Exchange is not really designed for this" area. First of all, if you want a reply to be sent on every mail, you have to use a rule, not the OOO/Autoreply option. In order to fire the rule, the mail should reach some mailbox which one depends on where you have configured the forwarding. For the latter, there are multiple ways it can be done, depending on what is the current state of John's mailbox. If the mailbox exists, "regular" forwarding should work fine, otherwise use a Transport rule. Another option is to use an Inbox rule, which of course again requires that the mailbox still exists. The delete action should also be done via an Inbox rule, and should be the last one set.

Have you considered simply assigning the address(es) John uses to another mailbox?