Why is that that order, and not the other? If it gave you the extra insurance first, and then consumed it, it would function correctly 100% of the time. This is an issue that literally only matters in the pocket circumstance of using up the insurance with your main character and then giving it to a teammate, and directly contradicts the Manual that says it will always be repaired for free for your teammates.
Come on guys, it's a bug.
I actually think it makes more sense the way it is. Perfecting the prompt means using an insurance for free, not repairing the skell. If there's no insurance left, it can't use it and thus you have to pay.
Maybe it's a bug, maybe it's not. Who gives a fuck.