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The answer is... 
The twenty dollar tip, that was given to the Dock Hand, shouldn't have been
added to the $270 price that the couples paid for the boat.
It should have been subtracted. The tip was already included in the $270 paid.

$90 + $90 + $90 = $270 - $20 (tip) = $250 (The actual cost of the boat)
$250 (Actual cost of the boat) + $50 (Amount returned by boat owner) = $300
$300 was the initial cost of the boat.