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1. I don't think it's possible for Issei to beat Loki yet, it took Issei, Akeno, Saji and Baraqiel combined effort to take Loki down, and the reason they got the opportunity is because of Saji's surprise appearance.
2. Nope. Again, Tannin is somewhere close to the Maou-class, Issei is only somewhere in the High-class Devil strength. He still can't beat Tannin in an all out fight.
3. Yes
4. Yes
5. Yes
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