even after lifting the curse on chester, he came back when I was in debt and offered to eat people and pay me, should that not happen after he's uncursed?
I think that's intentional. It's not like Chester can't eat people (he is a mimic after all), he just didn't want to be forced to eat people when he didn't want to. I don't see a problem if Chester still wants to pay you to eat people.
Yep, I noticed that as well. I feel like it should remove that as a possibility – after all, he says he might spend his gold on charity instead, so either he should just give you gold for free, or it should only have the devil appear to offer you a deal instead.