Unless he zero'd out his calipers on a bullet then he is fine.... That is how most of the guys on the shootout threads do it. Zero out on bullet and measure outside of the bullet hole.
Bluto, I think you're shooting tighter than you're giving yourself credit for.
I'm not sure I'm interpreting your second photo correctly.
To get your group spread you take outside-to-outside distance (of the soot or grease rings) of your farthest shots AND SUBTRACT A BULLET DIAMETER. This gives you the spread between bullet centers.
I'm fairly sure you're going to like how the 69s group. Even better (for 100 and 200 yards) may be flat-base benchrest bullets specifically built for itty-bitty groups from bolt action rifles.
Boat-tails will trump flat-base bullets once you start talking farther ranges and longer time-of-flight affected by wind.
Good shootin', Tex. let us know once you get your Fed 69s.