I also got the impression, that Roland had been there already the last time. It's still possible, that he forgot about it, since reincarnation scrambled his memories (that's the whole reason for his diaries). But it is doubtful the creator Goddess would leave such an obvious loophole. Also while Roland might have forgotten, his System (= Goddess of Order) would have remembered.

For a final boss this whore (literally as it seems) is quite a let-down. It looks like all she has is that weird talisman, however JP already *****slapped one system. I really doubt that talisman really has a 80% chance to work.