Sounds a bit like the Clipper around the world races ?
People pay a lot of money to act as crew with someone making all the decisions and calling the shots
Of course there is nothing to stop someone arranging and sorting their own trip as do many ferry pilots moving different machines through Africa
Some people like in sailing need to be part of such an organisation others want to be independent and control everything themselves whether in boats or planes
Kirk doesn't sound like a team player but more of the loan sailor type