I was raised under "who invites, pays". Now I am glad I got out of that mindset before I would meet a chick who wants to pay and argue with her.
If she is a student, or seems like her budget is low or lives only with one parent, I will just pay.
Sometimes I mention I enjoyed her company to kind of indicate that is one of the reasons I paid. And not "just because". Or I wil say she can pay the next time. Or if we are heading somewhere, like quick bite, I say that I pay the drink and she can pay the food.
When she clearly has a job, and looks professional, I usually struggle. Some girls offered to pay. Some are hesitant and I cannot really read it. There was this one girl where I misread it and even the waitress said ".. and the coffee and the muffin?" after I paid my own. And when we got out, the girl seemed much more distant. I pay when it's too busy around the bar, I pay when I really enjoy the company, I pay when the waitress gives sort of a expectation that I will pay everything, not to create some awkward moment. If I invited a girl something like a concert, I would tell her upfront that I will pay for it because it was my idea and it is a bit more pricy than a coffee. Had a date like that only once and she just told me that it is not a problem, she will pay her ticket and that it is a cool idea to go to X.
The disposable income I have after paying everything I need for the month is enough for like 130 dates anyways. And I have savings for thousands more. I have like 3 - 8 dated a month nowadays on average, so I not view money as not much of an issue.
Sometimes I even talk about the topic with girls. The girls I go out with are usually very aware of things and smart. So get her view on this and also set some basis for how we could handle finances if it goes more serious direction.
Anyways, the view on the whole investment thing... I would say what Chase wrote in that article is not "she should pay", but "be so charming, interesting and cool so that she feels like paying for the date is her part."