Cruised the Caribbean for 9 years from 1980-89 on a C&C Landfall 48. This was of course before GPS and the throngs of cruisers found today.
He hardly did any work himself but really knew how to sail. I asked him about breakdowns and repairs while cruising and he said he never had a problem he couldn't work around.
Me? I did almost everything until I just got tired of the whole thing. The boat bottom repainting was the first to go.