I'm sure I'm not getting the point about his loyalty, bearing in mind Anna is currently having sex with about 10 times as many people as he is. Plus, they're not actually in any kind of formal relationship, beyond being fuck buddies, which I'm sure doesn't preclude them seeing other people. Yes, Anna gets jealous, but then she gets insanely jealous if anyone shows the slightest bit of interest in anyone but her. Remember Alfred, when her and Rebecca were helping him in the garden, and he was staring at Rebecca's butt, because she wasn't wearing any panties. Anna got so jealous about that, simply because his attention wasn't on her, for a few minutes.
I'm not trying to make out that John is a saint, because he isn't. He obviously likes women, and playing the field. But Anna is doing exactly the same thing, just a lot more. So I fail to get the point you're trying to make? If he's a douchebag because of this, then she must be as well. And I don't think you're trying to suggest that, so there must be some other reason him being such a jerk in your eyes ( ie you simply don't like him)
And as for the money. If she doesn't tell him about it, then he doesn't know. Remember, Anna herself initially believed that the operation would be covered by Andrew's insurance, so why wouldn't John think the same, if Anna neglected to tell him?
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