George Takei always brings a smile with a thought, something about people stealing (who won't go to jail), and this is not where I'd be trippin...
Over the years I've seen a variety of folk eke out a comfortable cruising income as they cruised... Off hand, I'd say it is not that hard.
That said, those who are successful at it seem to fall within a certain mindset of not concentrating on a single thing (it seems that multiple small income streams work better than one big one), they're not reinventing the wheel, keep a low profile, and, most importantly, they're not greedheads. They also can tell when/where a need needs filling...
Then again, there are exceptions but the folks we've encountered who were making money and happy seemed to fall into that group.
A case in point: we knew a couple who were nearly flat broke in the Canaries and when a group of us were talking about fishing and handlines they seemed to take a keen interest. Next thing I knew he was asking me where to find the bits to make a handline...
As it happened, there used to be a fishermen's coop in Las Palmas that sold cheap commercial fishing line, rubber squids, associated hardware, and suchlike. So I took him to the coop and he bought enough stuff for a couple of handlines and lures...
A couple of days later, there he was by the ARC boats sitting on a bench making handlines like an old pro while a half dozen ARC folks stood in line with money in hand waiting to buy one.
A couple of weeks later they sailed off headed towards the Caribbean fully provisioned, cash enough for a while, and a whole lot of handline/lure making materials in a locker...
Listening to Telephone
So it goes...
Bruce+
9 hours ago