Caidin bought and restored to full airworthiness the oldest surviving Junkers Ju 52 aircraft, a Ju 52/3m, Serial № 5489, which he named Iron Annie.
Caidin also worked as a pilot for the movie The War Lover, flew with the U.S. Air Force Thunderbirds demonstration squadron for several months, and was made an honorary member of the U.S. Army's Golden Knights parachute demonstration team.