I know where you're coming from BEagle - in fact I think we have flown some of those together!
A lot of Squadrons in the RAF used to make a great deal of the fact that they had some pilots flying aircraft older than themselves. But at a flying training school somewhere in England in 1993, we went one better. We had an aircraft which was originally delivered to the RAF in 1949. One day our 24 year old QFI flew with a 19 year old student, making their combined age less than the age of the airframe!