If Southwest starts letting its passengers use Wi-Fi when the aircraft leaves the gate or soon thereafter that will amount to a lot more time online than other airlines are offering. That's more opportunity for increasing Wi-Fi fees, too.
Consumers don't want to be constricted on their own devices, even if they hold these devices 10,000 feet above ground. Charge for access, sure, but content or commerce behavior above ground will mirror their behavior on the ground.
Golden Eagle Acquisitions sees an opportunity in melding content and Wi-Fi technology, but Row 44's relatively small foothold may not make it the ideal tool for the blending experiment. Also, users will evolve more and more towards their own entertainment, so the content part will become redundant over time.