One of our delivery skipper friends commented that the reason he bought a Caribbean condo apartment when he lived on his boat and already owned 2 others was so he could rent it out to high season tourists so he wouldn't have to work so hard at his delivery business. My look of ??bemusement?? elicited the comment "It's a lifestyle, Jeanne."
The sailing/skippering/cruising lifestyle is not for everyone, but it IS a lifestyle that many are loathe to abandon.
However, crewing on a luxury yacht, of which there are many and which seem to be recession-proof (don't hold me to that), seems to pay quite well. There are a number of publications devoted to this area. One that I am familiar with is http://www.the-triton.com/
but I believe there are others.