Do you have enough seals to promote past recruit and then pay for the chocobo insurance? We still dont know how much it is to rank past recruit, or if you'll even have to do another quest once you turn in the seals toward that rank.
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There's been a lot of discussion about whether or not the requirements for obtaining a personal chocobo were too lax, or whether or not they should be more rigorous. I asked Yoshida about the reasoning behind the implementation and he said that his first and foremost goal is that everyone be able to easily make use of the new transportation methods.