Wouldn't Sawyer have expected the freighter to have sent another form of transport for him and the other Losties? Or that the helicopter could have been fixed (even temporarily) before it refuelled?
He could have whispered to Kate in case that didn't happen; but I don't think he had ruled being rescued permanently out of the equation.
It's quite a good strategy to send someone to smooth the path before his arrival at his daughter's door. After all, the mother has severe issues with Sawyer (quite rightly) and might not want to welcome Sawyer back into her life even for her daughter's sake.
Just another way of looking at it.
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