I don't think so. That is because the wire that is outside of the structure is a different wire than the one inside the structure in the hierarchy of LabVIEW objects. That is why you can delete a wire inside the structure without deleting the wire outside. If you click, double click, or triple click the wire, you can never also highlight the wire on the other side of the structure. They are two different wires that happen to wire into the same node that is the tunnel of the structure.
It might be possible to do some LabVIEW scripting to copy the description and tip of one wire to the other wire that might qualify based on them sharing the tunnel node or some other LabVIEW object. But in all honesty, I'm not sure it would be worth the trouble. The description/tip property of a wire is something I've never actually used though there may be some benefits in using it to document some special wires. But I tend to put free text labels next to it so the documentation is obvious just by looking at the block diagram.
