I have purchased a Chocobo for the maximum amount of time, but when this expires, I will need to purchase a new one. Will the levels be reset when i get a new Chocobo or will the progress i make on each one be stored so i dont need to do it again every time?
Yes, the levels you gain while riding a Chocobo are permanent. Next time you rent one out, the levels you gained from the first rental will persist.
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