Never tried managing a rotation, and what that does to your finances.
Women cost money. Days out to London, or Washington DC, or whatever to do really fun stuff can cost very good money. Not every girl gets that treatment, because it's not even possible.
Just like with weekends, you prioritise and put things where they are warranted based on good judgement. Not based on "being a gentleman".
A guy with rising standards through options, simply a woman turning up at your place willing to have sex with you doesn't warrant your cash as much. You start to judge whether she brought anything with her, or whether she just expected to raid your cupboards. Etc.
And you can tell really fast who is a mooch and who isn't. Doesn't take months.
I know many men who "manage a rotation". It can get expensive. I'm dating someone myself who has had as many as 7 women on rotation at once in the past. He said it was not only expensive, but exhausting (both physically and mentally) as well, lol.
There is nothing wrong with being a gentleman. I don't see gentlemanly behavior as supplicating "nice guy" behavior at all. A gentleman is someone whose company is desired by women, someone who behaves as an autonomous man, and someone who comports himself with class and refinement.
A gentleman would rarely allow himself to be seen with his lady paying his way. That makes him appear dependent, moochy, and as though he can't afford things. That is not how a solid man wishes to appear in front of other men.
I agree some women will warrant higher quality attention than others. But if OP is starting to go out in public with this chick, and she's already giving him sex...pay for the dates. Don't be a d o u c h e. Maybe she isn't LTR material but there is no need to be an ass.
I often offer to pick up the tab on first dates or early on dating. Men never take me up on that offer, almost without exception because of the dynamic of dependency that conjures. (They do not wish to appear dependent on a woman.) I will note that I date well established older men who see it as a point of pride to demonstrate financial strength and generosity. It is not about provider game. These men can afford things. They are not worried about paying for a $50 meal for 2. It's a different perspective. It's kind of like when I pick up the tab for a big family meal or host people in my home for the holidays. I do it because I choose to. It makes me happy to do it, and it is a generous gesture. Generosity comes from a position of strength is my point.
And I do agree that you can sniff out a mooch in short order. But dating with masculine/feminine polarity is different than mooching or dating in a transactional sense (I do or get X...you do or get Y).