"Well then, all the more reason to update the equipment if it ends up being worn out." He doesn't take any other connotation to it either, and rather moves on with the conversation.
"If that does happen, be sure to let someone know. It won't do any good if we never know what's broken."
Re: 1a
"If that does happen, be sure to let someone know. It won't do any good if we never know what's broken."