Anne ought to stop dwelling on that jerk Wentworth his was very much my feeling. I can understand Anne having no heart for anyone else for some time after the breakup, but when Wentworth failed to show up again after he had made some money I think a sensible woman would have cut her losses and tagged along with Lady Russell on her trips to Bath to check out alternative possibilities. Anne did not have to remain isolated at Kellynch, and by doing so she risked a perpetually loveless existence.

and encourage that nice Captain Benwick
I can't agree here. Consider Wentworth's characteristics - headstrong, lots of spirit and brilliancy, wit, an eager, outgoing character. If that is the sort of man who floats Anne's boat then I don't think Benwick is her type at all. Admittedly in the novel Benwick has been recently bereaved, but the Admiral, who has known him longer, describes him as "rather too piano", and as a suitable mate for Anne I'm inclined to agree.

This is going to look bad from a mercenary point of view
I have never for a moment thought that Anne was ever mercenary. The mercenary character is Lady Russell, and as I've posted before, I think her concerns were actually quite realistic. As for how things look regardless of Anne's actual motives, as I see it a major theme of the novel, explicit from page one, is the absurdity of placing value on rank and the appearance of wealth, as opposed to what truly matters, such as open heartedness and real affection.