Work a while to ease the boredom, travel a bit, spend the money on winches (and wenches), work a while, repeat. For as long as there is a demand for that sort of thing and the body and brain can do it, why not?
Splendid idea. During my time with Air Nauru in the late seventies (and more) I met a handy-man traveller who went by boat and occasional aeroplane between islands in the South Pacific. He used to fix old pedal operated Singer Sowing machines that had been used by missionaries on the islands. People would then ask him to fix other knick-knacks such as toasters, fridges and so on. He got free accommodation and meals wherever he went and made many friends with benefits among attractive nubiles en-route. (pun, Joyce...)