....had an uncle who did just that delivered yatchs....from Boston to the Caribbean at the beginning of the season and back at the end...airfare back and forth when not sailing and a fireman when home.
Made headlines once when he and his mate got caught buy a quick moving storm off the Carolinas...got rescued by an Irish freighter...went to Ireland and flew back home...happened back in the 80’s
...or it might have been early 90’
Did the yacht owners blame your uncle for the loss? Maybe thought he abandoned ship too soon?