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While there are certainly reimbursable skills that is not how things generally work in the cruising community...
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This is a good observation, Phil. In what I call the 'real" cruising community, reciprocal help is the norm, and
money is never exchanged. The skills that are present in the average popular anchorage are astounding, and by the time cruisers have been out for a few years, they understand the need for mutual support from within the group. It is amazing, and very gratifying to be part of.
I have no experience in the Caribe, but from reading lots of posts here on CF I believe that there are a lot of boats there that are not long term cruisers, and the behavior patterns may be different than here in the Pacific islands. This might mean more willingness to hire out
work... I dunno.
Finally, the locals may appear to be unworldly and naive, but they will have a very good idea about what goes on in the anchorage, let alone in a marina... and they will not be happy if visitors are taking over any jobs that they might otherwise be doing. Careful adherence to permits may satisfy the authorities, but we've heard of cases where local 'tradesmen" have expressed their unhappiness with poachers with violence. Not what most folks want to deal with!
Jim