Housesitting opportunities in places you'd like to visit are extremely rare. I used to live in a mountain resort town, and there were posts in our housing FB group every week seeking "housesitting opportunities" (read: free lodging during their ski vacation). No one ever replied.

Freighter cruising is much more expensive than flying for the same distance, but cheaper than an actual cruise. You could probably simulate the experience by living in a motel 6 with a stranger (since you won't get your own bunk) and getting food from Denny's 3x a day.