There was one thing I think Kaiki neglected to consider when he took the money: that Gaen knew he would take the money and do the job anyway.
After all, he was just thinking that he couldn't visit Nadeko more than five more times with his current funds the night before.
She could have given him those funds considering his troubling personality. It is what you would expect of a senior, and less what we would expect from her rather overbearing personality in the past. Or, thinking further, maybe we don't know Gaen as well as we think we do, like how we are finding out more about Kaiki now.
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