Cross-Country Road Trip in a '68 Barracuda

Yes. He can pigtail a new ignition switch under the column if it fails.

Not likely but can't hurt.
I did that for years till I got around to replacing the original one.
Changing a headlight switch can be a PITA.
But the work around is get off the road after dark.
That was my rule anyway for safety.
Night driving is exponentially more dangerous.