Jack and Kerry are different enough that I'd say even someone with Kerry could use a Jack. For a safe roll, Assassin+Extra is probably best since both are great for high difficulty. Waver and Tamamo are both excellent for that as well, probably better than what Assassin+Extra could offer. Of course you do have a chance to be spooked by Sanzang, but it's 1/3 so not that bad. You could use a better archer too, but Gil comes back next year so you could always roll for him then.
Summary: Assassin+Extra = safe, Caster = higher risk, higher return.
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